Relevant bibliographies by topics / C-C bonds

Academic literature on the topic 'C-C bonds'

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Published: 6 September 2023

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Journal articles on the topic "C-C bonds"

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RITTER, STEPHEN K. "EXTREME C–C BONDS." Chemical & Engineering News 87, no. 19 (May 11, 2009): 32–33. http://dx.doi.org/10.1021/cen-v087n019.p032.

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Huntley, Deborah R., Georgios Markopoulos, Patrick M. Donovan, Lawrence T. Scott, and Roald Hoffmann. "Squeezing CC Bonds." Angewandte Chemie 117, no. 46 (November 25, 2005): 7721–25. http://dx.doi.org/10.1002/ange.200502721.

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Huntley, Deborah R., Georgios Markopoulos, Patrick M. Donovan, Lawrence T. Scott, and Roald Hoffmann. "Squeezing CC Bonds." Angewandte Chemie International Edition 44, no. 46 (November 25, 2005): 7549–53. http://dx.doi.org/10.1002/anie.200502721.

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Zeng, Xiaoming, and Xuefeng Cong. "Chromium-Catalyzed Cross-Coupling Reactions by Selective Activation of Chemically Inert Aromatic C–O, C–N, and C–H Bonds." Synlett 32, no. 13 (May 11, 2021): 1343–53. http://dx.doi.org/10.1055/a-1507-4153.

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AbstractTransition-metal-catalyzed cross-coupling has emerged as one of the most powerful and useful tools for the formation of C–C and C–heteroatom bonds. Given the shortage of resources of precious metals on Earth, the use of Earth-abundant metals as catalysts in developing cost-effective strategies for cross-coupling is a current trend in synthetic chemistry. Compared with the achievements made using first-row nickel, iron, cobalt, and even manganese catalysts, the group 6 metal chromium has rarely been used to promote cross-coupling. This perspective covers recent advances in chromium-catalyzed cross-coupling reactions in transformations of chemically inert C(aryl)–O, C(aryl)–N, and C(aryl)–H bonds, offering selective strategies for molecule construction. The ability of low-valent Cr with a high-spin state to participate in two-electron oxidative addition is highlighted; this is different from the mechanism involving single-electron transfer that is usually assigned to chromium-mediated transformations.1 Introduction2 Chromium-Catalyzed Kumada Coupling of Nonactivated C(aryl)–O and C(aryl)–N Bonds3 Chromium-Catalyzed Reductive Cross-Coupling of Two Nonactivated C(aryl)–Heteroatom Bonds4 Chromium-Catalyzed Functionalization of Nonactivated C(aryl)–H Bonds5 Conclusions and Outlook
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Egami, Hiromichi. "Fluorofunctionalizations of C–C Multiple Bonds and C–H Bonds." Chemical and Pharmaceutical Bulletin 68, no. 6 (June 1, 2020): 491–511. http://dx.doi.org/10.1248/cpb.c19-00856.

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Meng, Ge, Pengfei Li, Kai Chen, and Linghua Wang. "Recent Advances in Transition-Metal-Free Aryl C–B Bond Formation." Synthesis 49, no. 21 (September 26, 2017): 4719–30. http://dx.doi.org/10.1055/s-0036-1590913.

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Arylboronic acids and their derivatives are widely used in organic synthesis. Conventional methods for their preparation require either reactive organometallic reagents or transition-metal-mediated processes. In recent years, transition-metal-free reactions for aryl C–B bond formation that obviate preformed organometallic reagents have gained interest and have developed rapidly. These new reactions have shown significant advantages for the preparation of functionalized molecules. In this review, an overview of the recent advances in transition-metal-free aromatic borylation reactions is provided.1 Introduction2 Transition-Metal-Free Transformations of CAr–N Bonds to CAr–B Bonds3 Transition-Metal-Free Transformations of CAr–X Bonds to CAr–B Bonds4 Transition-Metal-Free Transformations of CAr–H Bonds to CAr–B Bonds5 Conclusion
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Luh, Tien-Yau. "Chelation Assisted Conversion of C-S Bonds into C-C Bonds." Phosphorus, Sulfur, and Silicon and the Related Elements 120, no. 1 (January 1, 1997): 259–73. http://dx.doi.org/10.1080/10426509708545523.

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Hamel, Jean-Denys, and Jean-François Paquin. "Activation of C–F bonds α to C–C multiple bonds." Chemical Communications 54, no. 73 (2018): 10224–39. http://dx.doi.org/10.1039/c8cc05108a.

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Kaupp, Gerd, and Jürgen Boy. "Overlong CC Single Bonds." Angewandte Chemie International Edition in English 36, no. 12 (February 3, 1997): 48–49. http://dx.doi.org/10.1002/anie.199700481.

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Wang, Chang-Sheng, Pierre H. Dixneuf, and Jean-François Soulé. "Photoredox Catalysis for Building C–C Bonds from C(sp2)–H Bonds." Chemical Reviews 118, no. 16 (July 16, 2018): 7532–85. http://dx.doi.org/10.1021/acs.chemrev.8b00077.

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Dissertations / Theses on the topic "C-C bonds"

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Correia, Camille. "Oxidative C-C bond formation via metal-catalyzed coupling of two C-H bonds." Thesis, McGill University, 2013. http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=114441.

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This thesis describes the formation of new C-C bonds from the direct oxidative coupling of two C-H bonds, through the use of metal catalysts for activation. First, three different oxidative Cross-Dehydrogenative-Coupling (CDC) reactions will be presented. Initially, through the use of an organic co-catalyst, N-hydroxyphthalimide (NHPI), oxygen could be utilized as the terminal oxidant for the metal catalyzed alkylation of benzylic C-H bonds with 1,3-dicarbonyls and ketones in Chapter 2. The reaction was found to be feasible for a variety of substrates with readily enolizable C-H bonds. Next, the 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) mediated alkynylation of sp3 C-H bonds was studied. A novel copper (I) triflate catalyzed CDC reaction of unactivated benzylic C-H bonds and terminal aromatic alkynes is presented in Chapter 3. After further studies, the alkynylation of benzylic ethers could also be realized in the presence of a catalytic amount of silver (I) triflate, as described in Chapter 4. Both procedures were found to be amendable for aromatic terminal alkynes, however could not be extended to aliphatic alkynes. Finally, a palladium catalyzed Minisci-type reaction will be described in Chapter 6. Peroxide generated α-hydroxyalkyl radicals could be reacted with azines in moderate to good yields. A stoichiometric amount of acid, used in the traditional Minisci reaction, was replaced by a catalytic amount of palladium dichloride.
Cette thèse décrit la formation de nouvelles liaisons C-C par activation oxydative directe de deux liaisons C-H grâce à l'utilisation de métaux de transition comme catalyseurs. La première partie présentera trois différentes réactions de Cross-Dehydrogenative-Coupling (CDC) oxydantes. Dans un premier temps, sera présentée dans le chapitre 2, la réaction d'alkylation de liens C-H benzylique par 1,3-dicarbonyles et cétones. Ce system a démontré son efficacité sur une large variété de substrats contenant des liaisons C-H enolysable. De plus il a été rendu possible, grâce à l'utilisation d'un co-catalyseur organique, le N-Hydroxyphthalimide (NHPI), d'utiliser l'oxygène moléculaire comme oxydant terminal. Dans un second temps, nous étudierons l'utilisation du 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) comme médiateur pour l'alkynylation de liaisons sp3 C-H. Une nouvelle CDC réaction catalysée par le triflate de cuivre (I) sera présentée dans le chapitre 3, entre un alcyne et une liaison C-H benzylique. Le chapitre 4 présentera le développement de cette réaction à l'alcynation d'éthers benzyliques en présence d'une quantité catalytique de triflate d'argent (I). Ces deux procédures sont seulement applicables pour les alcynes vrais aromatiques. Finalement, le chapitre 6 portera sur la réaction de Minisci catalysée par le palladium. Le peroxyde radical α-hydroxyalkyl généré lors de la réaction est capable de réagir avec les azines. La quantité stœchiométrique d'acide nécessaire lors de la traditionnelle réaction de Minisci, a été remplacée par une quantité catalytique de dichloro palladium.
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Rix, Kathryn. "Electrochemical reduction of amides and c=c bonds." Thesis, Imperial College London, 2012. http://hdl.handle.net/10044/1/39846.

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Reduction of amides to amines is an important transformation in organic synthesis, which has been identified as among the 'top ten most important reactions' by a consortium of pharmaceutical companies. Presently achieved by hydride or borane reagents, it is both hazardous and generates excessive volumes of effluent and waste. Similarly, chemoselective reduction of C=C bonds, particularly conjugated double bonds, also presents a significant challenge in organic synthesis. Electrochemical synthesis using a flow reactor offers an environmentally benign and energy efficient technology for producing key intermediates in the synthesis of candidate drug molecules; its benefits include: improved control of reaction parameters, reproducibility and scalability. The first part of the thesis describes a study on the kinetics of the selective electrochemical reduction of C=C maleimide derivatives using a rotating disc electrode system. The resulting data was used to define the reactor's operating conditions. Subsequently, the chemoselective and stereoselective reduction of maleimide derivatives were carried out in the electrochemical flow reactor with a graphite felt cathode and the rate of reactant depletion, monitored by UV-visible spectroscopy. In the second part, amide reduction was studied in an electrochemical flow reactor using vitreous carbon and boron-doped diamond cathodes. The reduction of N,N- dimethylbenzamide produced the corresponding amine, benzaldehyde and benzyl alcohol. The selectivity of the reaction was investigated as a function of reaction conditions, and a mechanism for the reduction was proposed. Subsequently, a range of functionalised amides were subjected to electrochemical reduction under optimised conditions, to further assess the scope of the methodology as a tool for organic synthesis. The influence of electron donating and withdrawing groups incorporated in to N-benzoylpyrrolidine derivatives were investigated, as well as the pattern of substitution on the amides. The result revealed observable trends in the product distribution between the corresponding amine, benzaldehyde and benzyl alcohol compounds.
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Kanuru, Vijaykumar. "Understanding surface mediated C-C and C-N bond forming reactions." Thesis, University of Cambridge, 2010. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.608956.

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Bowen, John George. "C-H activation in the formation of C-N and C-O Bonds." Thesis, University of Bristol, 2015. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.685335.

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The regioselective activation of C-H bonds and subsequent transformation into desirable functional groupS is an attractive prospect in organic synthesis. We have developed two novel C-H functionalisation reactions; the first is an intramolecular, sulfonamide directed, C-H amination reaction for the synthesis of 3_phenylisoindolinone derivates and the second is a sulfonamide directed ortho C-H acetoxylation reaction. Both isoindolinones and phenol derivatives of sulfonamides are important motifs in numerous pharmaceutically relevant compounds. The Cull-catalysed intramolecular C-H amination reaction for the synthesis of substituted 3-phenylisolindolinone derivatives (Scheme i) was found to be tolerant to substitution on both aromatic rings, however, no reaction was observed on exchanging the tethered aryl group for an alkyl group. Mechanistic investigations revealed that C-H cleavage was not part of the rate-determining step which is likely to be coordination of the copper catalyst to the sulfonyl amide. Substitution of the tethered phenyl ring (R2 ) and a subsequent Hammett analysis indicated that this coordination may be accelerated by a cation-IT interaction between CU11 and the pie system of the aryl group.
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Lee, Kang-sang. "New Concepts and Catalysts for Enantioselective Synthesis of C-C, C-Si, and C-B Bonds." Thesis, Boston College, 2010. http://hdl.handle.net/2345/1739.

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Thesis advisor: Amir H. Hoveyda
Chapter 1. The development of chiral monodentate N-heterocyclic carbenes (NHCs) is presented. Structurally varied twenty-eight new chiral imidazolinim salts, NHC precursors, were synthesized and characterized. Chapter 2. The first example of Cu-catalyzed enantioselective conjugate additions of alkyl- and arylzinc reagents to unactivated cyclic enones is presented. Transformations are promoted in the presence of 2.5-15 mol % of a readily available chiral NHC-based Cu complex, affording the desired products bearing all-carbon quaternary stereogenic centers in 67-98% yield and in up to 97% ee. Catalytic enantioselective reactions can be carried out on a benchtop, with undistilled solvent and commercially available (not further purified) Cu salts. Chapter 3. A new class of enantioselective conjugate addition (ECA) reactions that involve aryl- or alkenylsilylfluoride reagents and are catalyzed by chiral non-C2-symmetric Cu-based NHC complexes are presented. Transformations have been designed based on the principle that a catalytically active chiral NHC-Cu-aryl or NHC-Cu-alkenyl complex can be accessed from reaction of a Cu-halide precursor with in situ-generated aryl- or alkenyl-tetrafluorosilicate. Reactions proceed in the presence of 1.5 equivalents of the aryl- or alkenylsilane reagents and 1.5 equivalents of tris(dimethylamino)sulfonium difluorotrimethylsilicate. Desired products are isolated in 63-97% yield and 73.5:26.5-98.5:1.5 enantiomeric ratio (47%-97% ee). Chapter 4. An efficient Cu-catalyzed protocol for enantioselective addition of a dimethylphenylsilanyl group to a wide range of cyclic and acyclic unsaturated ketones, esters, acrylonitriles and dienones is presented. Reactions are performed in the presence of 1-5 mol % of commercially available and inexpensive CuCl, a readily accessible monodentate imidazolinium salt as well as commercially available (dimethylphenylsilyl)pinacolatoboron. Cu-catalyzed 1,4- and 1,6-conjugate additions afford the enantiomerically enriched silanes in 72%-98% yield and 90:10->99:1 enantiomeric ratio (er) with up to >25:1 of Z:E selectivity. Chapter 5. A Cu-catalyzed method for enantioselective boronate conjugate additions to trisubstituted alkenes of acyclic a,b-unsaturated carboxylic esters, ketones, and thioesters is presented. All transformations are promoted by 5 mol % of a chiral monodentate NHC-Cu complex, derived from a readily available C1-symmetric imidazolinium salt, and in the presence of commercially available bis(pinacolato)diboron. Reactions are efficient (typically, 60% to >98% yield after purification) and deliver the desired boryl carbonyls in up to >98:2 enantiomer ratio (er). In addition, metal-free, nucleophilic activation of a B-B bond has been exploited in the development of a highly efficient method for conjugate additions of commercially available bis(pinacolato)diboron to cyclic or acyclic a,b-unsaturated carbonyls. Reactions are readily catalyzed by 2.5-10 mol % of a simple NHC. A variety of cyclic and acyclic unsaturated ketones and esters can serve as substrates. Transformations deliver boryl carbonyls bearing tertiary as well as quaternary B-substituted carbons in up to >98% yield
Thesis (PhD) — Boston College, 2010
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry
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Owen, Gareth Richard. "Palladium-mediated transformationand activation of unsaturated C-N, C-S and C-O bonds." Thesis, Imperial College London, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.408281.

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Jiang, Tuo. "Palladium(II)-Catalyzed Oxidative Carbocyclization : Stereoselective Formation of C–C and C–B Bonds." Doctoral thesis, Stockholms universitet, Institutionen för organisk kemi, 2014. http://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-108669.

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Transition metal catalysis has emerged as one of the most versatile methods for the selective formation of carbon–carbon and carbon–heteroatom bonds. In particular, oxidative carbon–carbon bond forming reactions have been widely studied due to their atom economic feature. This thesis has been focused on the development of new palladium(II)-catalyzed carbocyclization reactions under oxidative conditions. The first part of the thesis describes the palladium(II)-catalyzed oxidative carbocyclization-borylation and -arylation of enallenes. In these reactions, the (σ-alkyl)palladium(II) intermediate, which was shown previously to undergo β-hydride elimination, could be trapped in situ by organoboron reagents (B2pin2 and arylboronic acids) to form new carbon–boron and carbon–carbon bonds. Through these two protocols, a range of borylated and arylated carbocycles were obtained as single diastereomers in high yields. The second part deals with a palladium(II)-catalyzed oxidative diarylative carbocyclization of enynes. The reaction was proposed to start with a syn-arylpalladation of an alkyne, followed by insertion of the coordinated alkene. Subsequent arylation afforded a series of valuable diarylated tetrahydrofuran and tetrahydropyran products. The final part of the thesis advances the previously developed palladium(II)-catalyzed oxidative carbocyclization-borylation of enallenes in an enantioselective manner. C2-symmetric chiral phosphoric acids were used as the novel co-catalyst to trigger the enantioselective formation of intramolecular carbon–carbon bonds. By using this chiral anion strategy, a number of enallenes were converted to the borylated carbocycles with high to excellent enantioselectivity.

At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 4: Manuscript.

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Ziadi, Asraa. "Metal-catalyzed functionalization of c-c bonds in four-membered rings." Doctoral thesis, Universitat Rovira i Virgili, 2014. http://hdl.handle.net/10803/320185.

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En els darrers anys, la funcionalització catalítica d´enllaços C-C ha suscitat un gran interés, essent una de les disciplines amb més potencial en química organometàlica. Aquesta tesi doctoral es basa en el repte de dissenyar nous mètodes catalítics de functionalitazió d´enllaços C-C en anells de cuatre baules. Específicament, s´ha demostrat la viabilitat per preparar cetones γ-arilades via rotura d´enllaços C-C catalitzada per Pd en anells de tert-ciclobutanol utilitzant clorur d´aril i tosilats (Capítol 2). La transformació presenta una gran generalitat amb càrregues de catalitzador molt baixes. Tanmateix, s´ha trobat que fosfines riques en electrons i impedides estèricament permeten evitar processos destructius de β-eliminació d´hidrògen. Amb els precedents del capítol 2, s´ha extés satisfactòriament la generalitat de la reacció de rotura d´enllaços C-C d´anells de tert-ciclobutanol mitjançant l´acoplament amb haloacetilens per donar lloc a cetones amb grups alquins en posició γ (Capítol 3). Curiosament, els substituents del grup alquí tenen una gran influencia en la reacció. És certament remarkable l´interés potencial de la metodologia ja que els productes finals poden ser transformats fàcilment en productes d´alt valor afegit mitjançant reaccions d´acoplament creuat. Al Capítol 4, s´ha pogut extendre les metodologies de trencament d´enllaços C-C en anells de cuatre baules mitjançant el desenvolupament d´una metodologia catalitzada per Ni entre benzociclobutanones i diens per donar lloc a cicloadicions [4+4]. El mètode va mostrar una preferència específica per la formació d´anells de vuit baules respecte la formació d´anells de sis baules. Aquesta tesi doctoral també ha estudiat el disseny de metodologies de fixació de CO2 i formació d´enllaços C-F mitjançant activació catalítica d´enllaços C-C (Capítol 5). Tot i que no s´han trobat condicions de reacció òptimes, el nostre grup de recerca està actualment involucrat en el disseny de metodologies semblants i s´espera que aquesta recerca permeti el disseny de processos de fixació de CO2 i formació d´enllaços C-F mitjançant trencament C-C en un futur no molt llunyà.
Recientemente la funcionalización catalítica de enlaces C-C ha suscitado un gran interés en la comunidad científica a pesar de los retos que conlleva. Esta tesis doctoral se ha basado en diseñar nuevos procesos catalíticos para la funcionalización de enlaces C-C en anillos de cuatro miembros. Específicamente, se ha demostrado la viabilidad de preparar cetonas con grupos arilo en posición γ usando precatalizadores de Pd para promover la rotura de enlaces C-C en anillos de tert-ciclobutanol utilizando cloruros de arilo y tosilatos como agentes arilantes (Capítulo 2). La transformación se caracteriza por su amplia generalidad y baja carga de catalizador. La selectividad de la reacción puede ser fácilmente controlada por la naturaleza del ligando, en la que fosfinas con grupos ricos en electrones y voluminosos dan los mejores resultados, evitando la β-eliminación de hidrógeno de las especies organometálicas intermedias. Considerando los precedentes del Capítulo 2, se ha extendido esta metodología al acoplamiento con haloacetilenos para preparar cetonas con grupos alquino en posición γ (Capítulo 3). Curiosamente, los substituyentes del grupo alquino juegan un papel fundamental en la reactividad, pudiéndose controlar mediante la utilización de un cierto ligando. En el Capítulo 4, se ha desarrollado una nueva transformación basada en una reacción catalizada por compuestos de Ni para efectuar la síntesis de anillos de ocho eslabones mediante una reacción formal de cicloadición [4+4] de benzociclobutanonas y dienos simples. Curiosamente, dicho método muestra una especial preferencia para formar anillos de ocho eslabones sobre los, a priori, anillos de 6 eslabones que son más estables termodinámicamente. En la presente tesis doctoral se ha estudiado también la viabilidad de llevar a cabo una fijación catalítica de CO2 y la formación de enlaces C-F mediante una rotura de enlaces C-C (Capítulo 5) aunque no se han encontrado las condiciones óptimas para llevar a cabo tales transformaciones.
The means to promote catalytic C-C bond-functionalization has gained a considerable attention in recent years and probably can be considered one of the most challenging and vibrant subjects in organometallic chemistry. This PhD thesis deals with the design of new metal-catalyzed functionalization of C-C bonds in four-membered ring frameworks. Specifically, we have demonstrated the viability of preparing γ-arylated ketones via Pd-catalyzed cleavage of C-C bonds in tert-cyclobutanol using aryl chloride or tosylate counterparts (Chapter 2). The transformation possesses a wide substrate scope and remarkable low catalyst loadings. Selectivity was controlled by the ligand in which electron-rich and sterically-hindered phosphine ligands provided a unique reaction outcome that avoided the proclivity of alkyl metal species towards destructive β−hydride elimination. Prompted by the precedents in Chapter 2, we successfully extended the scope of the metal-catalyzed C-C bond-cleavage of tert-cyclobutanols by using halo acetylene counterparts giving γ-alkynylated ketones (Chapter 3). Interestingly, substituents on the alkyne motif showed a remarkable influence on reactivity. Of particular interest is the application profile of such methodology since γ-alkynylated ketones could promote consecutive metal-catalyzed transformations into valuable synthetic intermediates. In Chapter 4, we extended the interest for C-C bond-cleavage beyond the use of tert-cycñobutanols. Specifically, we developed a Ni-catalyzed C-C bond-cleavage event in benzocyclobutenones for preparing eight-membered rings via formal [4+4]-cycloaddition with dienes (Chapter 4). The method shows a specific preference for eight-membered rings over thermodynamically more stable six-membered rings. This PhD thesis has also studied the development of catalytic CO2 fixation and C-F bond-formation via C-C bond-cleavage (Chapter 5). While we have not found reaction conditions to effect the desired transformations, our research group is actively involved in related catalytic endeavors and it is expected that such research will shed light into the targeted CO2 fixation or C-F bond-forming reactions via C-C bond-cleavage.
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Sau, Roca Míriam. "From Click Chemistry to catalytic cleavage of unstrained C-C bonds." Doctoral thesis, Universitat Rovira i Virgili, 2016. http://hdl.handle.net/10803/396080.

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Aquesta tesi doctoral es basa principalment amb la síntesis de molècules petites potencialment útils per investigacions avançades. S'han utilitzat diferents metodologies per obtenir-les: 1) Cicloaddicions intramoleculars entre un alkí i una azida lliures de coure per l'obtenció de derivats de benzodiazepines. Obtenint-se una gran varietat de triazols fusionats a heterocicles de set membres. Posteriorment, s'han dut a terme proves d'activitat biològica. 2) a) Trencament d'enllaços carboni-carboni no activats d'amino alcohols i utilització d'aquest com a nucleòfil juntament amb bromurs d'aril en una reacció d'acoplament catalitzada per pal.ladi per l'obtenció de dibenzil amines. S'ha dut a terme una gran optimització dels diferents paràmetres de reacció; base, dissolvent, electròfil, temperatura, catalitzador i lligand. b) Trencament d'enllaços carboni-carboni no activats de N-alil amino alcohols i utilització d'aquest com a nucleòfil juntament amb bromurs d'aril en una reacció d'acoplament catalitzada per pal.ladi per l'obtenció d'aldehids arilats en la posició beta. S'ha dut a terme la síntesis d'un gran nombre d' amino alcohols nous i aquests han estat sotmesos a les condicions optimitzades de reacció. Demostrant que aquest transformació és útil per un gran ventall de substrats (bromurs d'aril i amino alcohols).L'enamina resultant de la reacció d'acoplament s'ha aconseguit alquilar amb vinil metil cetona amb bons rendiments però pobres diastereoselectivitats tot i així s'ha demostrant que la reacció és factible. Per finalitzar, s'ha aconseguit desenvolupar la versió enantioselectiva de l’anterior transformació obtenint bons excessos enantiomerics tot i que baixos rendiments.
Ésta tesis doctoral está basada principalmente en la síntesis de moléculas pequeñas potencialmente útiles para investigaciones avanzadas. Se han empleado diferentes metodologías para obtenerlas: 1) Cicloadiciones intramoleculares entre un alkino y una azida libres de cobre para la obtención de derivados de benzodiazepinas. Se han obtenido una gran variedad de triazoles fusionados a heterociclos de siete miembros. Posteriormente se han realizado pruebas de actividad biológica de las moléculas resultantes. 2) a) Escisión de enlaces carbono-carbono no activados de amino alcoholes y utilitzación de éstos como nucleófilos conjuntamente con bromuros de arilo para una reacción de acoplamiento catalizada por paladio para la obtención de derivados de dibenzil aminas. Se ha realizado una gran optimización de las condiciones de reacción; base, disolvente, electrófilo, temperatura, catalizador y ligando. b) Escisión de enlaces carbono-carbono no activados de N-alilo amino alcoholes y la utilización de éste como nucleófilo conjuntamente con bromuros de arilo en una reacción de acoplamiento catalizada por paladio para la obtención de aldehídos arilados en posición beta. Se ha realizado la síntesis de un gran numero de amino alcoholes nuevos y éstos se han sometido a las condiciones optimizadas de reacción. Demostrando que ésta transformación es útil para una gran variedad de sustratos (bromuros de arilo y amino alcoholes). La enamina resultante de la reacción de acoplamiento se ha alquilado con vinil metil cetona con buenos rendimientos pero pobres diastereoselectividades aunque se ha demostrado que la reacción es factible. Para finalizar, se ha desarrollado la versión enantioselectiva de la anterior transformación obteniendo buenos excesos enantioméricos aunque con bajos rendimientos.
This PhD thesis is based basically on synthesis of small molecules potentially useful for further investigations. Different strategies have been used to obtain them; 1) Copper free intramolecular cycloadditions between an azide and an akyne for the obtention of benzodiazepine derivatives. A wide range of triazoles fused to seven membered heterocycles rings have been obtained. Later, biological studies have been carried out. 2)a) Carbon-carbon bond cleavage of amino alcohols has been carried out with the subsequent use of them as a nucleophile together with aryl bromides to develop a cross-coupling reaction for the obtention of dibenzyl amines. A wide optimization of the reaction parameters was carried out; base, ligand, catalyst, electrophile, temperatura, and solent. b) Carbon-carbon bond cleavage of N- allyl amino alcohols has been carried out with the subsequent use of them as a nucleophile together with aryl bromides to develop a cross-coupling reaction for the obtention of beta arylated aldehydes. An important number of new amino alcohols have been synthesized and these have been subjected to the optimized reaction conditions. It has been demonstrated that this transformation is useful for a wide range of substrates (amino alcohols and aryl bromides). The resultant enamine has been alkylated with methyl vinyl ketone with good yields but poor diastereoselectivity. To finish the enantioselective version of beta functionalization of aldehydes has been developed obtaining good enantioselectivity but poor yields
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10

Chudasama, V. "The use of aerobic aldehyde C-H activation for the construction of C-C and C-N bonds." Thesis, University College London (University of London), 2011. http://discovery.ucl.ac.uk/1324525/.

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This thesis describes a series of studies directed towards the use of aerobic aldehyde C-H activation for the construction of C-C and C-N bonds by the process of hydroacylation. Chapter 1 provides an introduction to the research project and an overview of strategies for hydroacylation. Chapter 2 describes the application of aerobic aldehyde C-H activation for the hydroacylation of vinyl sulfonates and sulfones. A discussion on the mechanism of the transformation, the effect of using aldehydes with different oxidation profiles and the application of chiral aldehydes is also included. Chapter 3 describes the functionalisation of γ-keto sulfonates with particular emphasis on an elimination/conjugate addition strategy, which provides an indirect approach to the hydroacylation of electron rich alkenes. Chapters 4 and 5 describe the application of aerobic aldehyde C-H activation towards the hydroacylation of α,β-unsaturated esters and vinyl phosphonates, respectively. An in-depth discussion on the mechanism and aldehyde tolerance of each transformation is also included. Chapter 6 describes acyl radical approaches towards C-N bond formation with particular emphasis on the synthesis of amides and acyl hydrazides.
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Books on the topic "C-C bonds"

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Li, Chao-Jun, ed. From C-H to C-C Bonds. Cambridge: Royal Society of Chemistry, 2014. http://dx.doi.org/10.1039/9781782620082.

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Shimajiri, Takuya. The Nature of Ultralong C–C Bonds. Singapore: Springer Nature Singapore, 2023. http://dx.doi.org/10.1007/978-981-99-0670-3.

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Lu, Wenjun, and Lihong Zhou. Oxidation of C─H Bonds. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2017. http://dx.doi.org/10.1002/9781119092490.

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You, Shu-Li, ed. Asymmetric Functionalization of C-H Bonds. Cambridge: Royal Society of Chemistry, 2015. http://dx.doi.org/10.1039/9781782621966.

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Goldberg, Karen I., and Alan S. Goldman, eds. Activation and Functionalization of C—H Bonds. Washington, DC: American Chemical Society, 2004. http://dx.doi.org/10.1021/bk-2004-0885.

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C-X bond formation. Heidelberg: Springer, 2010.

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Taillefer, Marc, and Dawei Ma, eds. Amination and Formation of sp2 C-N Bonds. Berlin, Heidelberg: Springer Berlin Heidelberg, 2013. http://dx.doi.org/10.1007/978-3-642-40546-4.

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1945-, Fuchs Philip L., ed. Reagents for direct functionalization of C-H bonds. Chichester, England: John Wiley, 2007.

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Zucherman, Jerry J. The Formation of bonds to C, Si, Ge, Sn, Pb (part 2). New York, N.Y: VCH Publishers, 1989.

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Catalyst Design for the Ionic Hydrogenation of C=N Bonds. [New York, N.Y.?]: [publisher not identified], 2015.

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Book chapters on the topic "C-C bonds"

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Kakiuchi, Fumitoshi. "Catalytic Addition of C – H Bonds to C – C Multiple Bonds." In Topics in Organometallic Chemistry, 1–33. Berlin, Heidelberg: Springer Berlin Heidelberg, 2007. http://dx.doi.org/10.1007/3418_2007_064.

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Treichel, P. M. "Reactions Involving C-H and C-C Bonds." In Inorganic Reactions and Methods, 230–32. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2007. http://dx.doi.org/10.1002/9780470145296.ch199.

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Bougioukou, Despina J., and Jon D. Stewart. "Reduction of CC Double Bonds." In Enzyme Catalysis in Organic Synthesis, 1111–63. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2012. http://dx.doi.org/10.1002/9783527639861.ch27.

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Bühler, Bruno, Katja Bühler, and Frank Hollmann. "Oxyfunctionalization of CC Multiple Bonds." In Enzyme Catalysis in Organic Synthesis, 1269–324. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2012. http://dx.doi.org/10.1002/9783527639861.ch31.

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Rios, Ramon, Jorge Esteban, and Xavier Companyó. "Cascade Reactions Forming C-C Bonds." In Stereoselective Organocatalysis, 351–80. Hoboken, New Jersey: John Wiley & Sons, Inc., 2013. http://dx.doi.org/10.1002/9781118604755.ch10.

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Shimajiri, Takuya. "Discovery of Flexible Bonds Based on an Extremely Elongated C–C Single Bond." In The Nature of Ultralong C–C Bonds, 41–78. Singapore: Springer Nature Singapore, 2023. http://dx.doi.org/10.1007/978-981-99-0670-3_3.

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Ghosh, Pradip, Marc-Etienne Moret, and Robertus J. M. Klein Gebbink. "Catalytic Oxygenation of CC and CH Bonds." In Non-Noble Metal Catalysis, 355–89. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2018. http://dx.doi.org/10.1002/9783527699087.ch14.

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"4. C–C bonds." In High Pressure Organic Synthesis, 93–128. Berlin, Boston: De Gruyter, 2019. http://dx.doi.org/10.1515/9783110556841-004.

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"C–C Bond Formation." In Biocatalysis in Organic Synthesis: The Retrosynthesis Approach, 217–53. The Royal Society of Chemistry, 2018. http://dx.doi.org/10.1039/bk9781782625308-00217.

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This chapter covers enzyme classes that are capable of catalysing reactions to form carbon–carbon bonds, including aldolases, hydroxynitrile lyases, thiamine-dependent lyases, terpene cyclases, carboxylases, Pictet–Spenglerases, P450 monooxygenase variants and methyltransferases. The chapter is divided into separate sections, each detailing the formation of carbon–carbon bonds by a specific enzyme class. Each section begins with a review of chemical methods of carrying out similar transformations, followed by a description of the enzyme class itself. The substrate scope of each enzyme class, including its chemo-, regio- and stereoselectivity, is discussed and a general mechanism for the enzyme-catalysed reaction is presented. This should give the reader a good understanding of when and how to carry out carbon–carbon bond forming reactions using enzymes.
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"C." In Encyclopedia of Municipal Bonds, 28–42. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2012. http://dx.doi.org/10.1002/9781118531624.ch3.

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Conference papers on the topic "C-C bonds"

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Mbomson, Ifeoma G., Scott McMeekin, Richard De La Rue, and Nigel P. Johnson. "Matching plasmon resonances to the C=C and C-H bonds in estradiol." In SPIE BiOS, edited by Tuan Vo-Dinh and Joseph R. Lakowicz. SPIE, 2015. http://dx.doi.org/10.1117/12.2081409.

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Parsch, Jörg, and Joachim W. Engels. "C–F···H–C hydrogen bonds in crystals of fluorobenzene ribonucleosides." In XIth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 1999. http://dx.doi.org/10.1135/css199902011.

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THORPE, M. F., BRANDON M. HESPENHEIDE, YI YANG, and LESLIE A. KUHN. "FLEXIBILITY AND CRITICAL HYDROGEN BONDS IN CYTOCHROME C." In Proceedings of the Pacific Symposium. WORLD SCIENTIFIC, 1999. http://dx.doi.org/10.1142/9789814447331_0018.

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Siewert, Inke. "Electroreduction of C=O Bonds in CO2, Ketones, and Aldehydes." In MATSUS23 & Sustainable Technology Forum València (STECH23). València: FUNDACIO DE LA COMUNITAT VALENCIANA SCITO, 2022. http://dx.doi.org/10.29363/nanoge.matsus.2023.032.

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ŽENÍŠEK, Jaroslav, Pavel SOUČEK, Pavel ONDRAČKA, and Petr VAŠINA. "STUDY OF W-X BONDS IN AMORPHOUS W-B-C." In NANOCON 2021. TANGER Ltd., 2021. http://dx.doi.org/10.37904/nanocon.2021.4380.

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saki, zeinab, Nahla Talebi, Abedin Zabardasti, and Ali Kakanejadifard. "The B–C and C–C bonds as preferred electron source for H-bondand Li-bond interactions in complex pairing of C4B2H6 with HFand LiH molecules." In The 20th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2016. http://dx.doi.org/10.3390/ecsoc-20-e018.

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Rollier, Floriane, Marta Costa Figueiredo, and Emiel Hensen. "The influence of copper particle size on the electrochemical reduction of CO to products with C-C bonds." In Materials for Sustainable Development Conference (MAT-SUS). València: FUNDACIO DE LA COMUNITAT VALENCIANA SCITO, 2022. http://dx.doi.org/10.29363/nanoge.nfm.2022.074.

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Zárate, Cayetana, and Rubén Martin. "Ni-Catalyzed Silylation of Inert C-O Bonds under Mild Conditions." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_2013101312526.

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Marco de Lucas, M. C., J. M. Chappé, L. Cunha, C. Moura, J. F. Pierson, L. Imhoff, V. Potin, et al. "Structure and Chemical Bonds in Black Ti(C, N, O) Thin Films." In XXII INTERNATIONAL CONFERENCE ON RAMAN SPECTROSCOPY. AIP, 2010. http://dx.doi.org/10.1063/1.3482693.

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Costa, Roberta L. da, and Simon J. Garden. "Phenanthridine derivatives via palladium catalyzed intramolecular functionalization of C(sp2)-H bonds." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_2013819134214.

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Reports on the topic "C-C bonds"

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Novoa, J. J., Myung-Hwan Whangbo, and J. M. Williams. Intermolecular interactions involving C-H bonds, 3, Structure and energetics of the interaction between CH{sub 4} and CN{sup {minus}}. Office of Scientific and Technical Information (OSTI), December 1991. http://dx.doi.org/10.2172/10187953.

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Gland, J. L. Hydrogen induced C-C, C-N, and C-S bond activation on Pt and Ni surfaces. Office of Scientific and Technical Information (OSTI), December 1992. http://dx.doi.org/10.2172/10102894.

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Gland, J. L. Hydrogen induced C-C, C-N, and C-S bond activation on Pt and Ni surfaces. Office of Scientific and Technical Information (OSTI), January 1992. http://dx.doi.org/10.2172/6915688.

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Gland, J. L. Hydrogen Induced C-C, C-N, & C-S Bond Activation on Pt & Ni Surfaces. Office of Scientific and Technical Information (OSTI), July 2004. http://dx.doi.org/10.2172/830711.

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Gland, J. L. [Hydrogen induced C-C, C-N, and C-S bond activities on Pi and Ni surfaces]: Summary. Office of Scientific and Technical Information (OSTI), December 1994. http://dx.doi.org/10.2172/10110807.

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Biermann, Ursula, and Jürgen O. Metzger. Functionalization of Unsaturated Fatty Compounds Across the C,C Double Bond. AOCS, May 2011. http://dx.doi.org/10.21748/lipidlibrary.39193.

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Lees, Alistair J. Photochemistry of Intermolecular C-H Bond Activation Reactions. Office of Scientific and Technical Information (OSTI), June 2000. http://dx.doi.org/10.2172/761218.

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McFarland, Eric, Horia Metiu, and Michael Gordon. Fundamental Mechanisms of C-X bond Transformations on Complex Molten Surfaces. Office of Scientific and Technical Information (OSTI), July 2019. http://dx.doi.org/10.2172/1580080.

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Asplund, M. C. Time resolved infrared studies of C-H bond activation by organometallics. Office of Scientific and Technical Information (OSTI), June 1998. http://dx.doi.org/10.2172/290889.

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Kimura, Mineo. Correlation between shape resonance energies and C-C bond length in carbon-containing molecules: Elastic electron scattering and carbon K-shell excitation by photons. Office of Scientific and Technical Information (OSTI), June 1994. http://dx.doi.org/10.2172/10159440.

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