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Artykuły w czasopismach na temat "Directed borylation"
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Wang, Yan, Le Wang, Ling-Yan Chen, Pinaki S. Bhadury i Zhihua Sun. "Transition Metal-Free Synthesis of Pinacol Arylboronate: Regioselective Boronation of 1,3-Disubstituted Benzenes". Australian Journal of Chemistry 67, nr 4 (2014): 675. http://dx.doi.org/10.1071/ch13642.
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The regioselective synthesis of pinacol arylboronate has been achieved from 1,3-disubstituted benzene through directed ortho-metallation (DoM)–borylation sequence. A wide range of substituents and borylating reagents were investigated. In situ lithiation and subsequent boronation predominantly occurred at the ortho-position to afford the desired products in moderate yields.
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Al Mamari, Hamad H. "Ir-Catalyzed ortho-C-H Borylation of Aromatic C(sp2)-H Bonds of Carbocyclic Compounds Assisted by N-Bearing Directing Groups". Reactions 5, nr 2 (1.05.2024): 318–37. http://dx.doi.org/10.3390/reactions5020016.
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C-H borylation is a powerful strategy for the construction of C-B bonds due to the synthetic versatility of C-B bonds. Various transition metals affect the powerful functionalization of C-H bonds, of which Ir is the most common. Substrate-directed methods have enabled directed Ir-catalyzed C-H borylation at the ortho position. Amongst the powerful directing groups in Ir-catalyzed C-H borylation are N-containing carbocyclic systems. This review covers substrate-directed Ir-catalyzed ortho-C-H borylation of aromatic C(sp2)-H bonds in N-containing carbocyclic compounds, such as anilines, amides, benzyl amines, hydrazones, and triazines.
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Iqbal, S. A., K. Yuan, J. Cid, J. Pahl i M. J. Ingleson. "Controlling selectivity in N-heterocycle directed borylation of indoles". Organic & Biomolecular Chemistry 19, nr 13 (2021): 2949–58. http://dx.doi.org/10.1039/d1ob00018g.
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N-Heterocycle directing groups lead to selective borylation of indole at C2 or C7 controlled by heterocycle ring size. With five membered heterocycle directing groups, C2 borylation is disfavoured due to an increased degree of distortion.
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Auth, Marin R., Kathryn A. McGarry i Timothy B. Clark. "Phosphorus‐Directed C−H Borylation". Advanced Synthesis & Catalysis 363, nr 9 (30.03.2021): 2354–65. http://dx.doi.org/10.1002/adsc.202100173.
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Cazorla, Clément, Timothy S. De Vries i Edwin Vedejs. "P-Directed Borylation of Phenols". Organic Letters 15, nr 5 (marzec 2013): 984–87. http://dx.doi.org/10.1021/ol303203m.
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Iqbal, S. A., J. Pahl, K. Yuan i M. J. Ingleson. "Intramolecular (directed) electrophilic C–H borylation". Chemical Society Reviews 49, nr 13 (2020): 4564–91. http://dx.doi.org/10.1039/c9cs00763f.
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Ros, A., R. Fernández i J. M. Lassaletta. "Functional group directed C–H borylation". Chem. Soc. Rev. 43, nr 10 (2014): 3229–43. http://dx.doi.org/10.1039/c3cs60418g.
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Xu, Ming-Hua. "Metal-free directed C–H borylation". Chinese Science Bulletin 65, nr 5 (1.02.2020): 331–33. http://dx.doi.org/10.1360/tb-2019-0657.
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De Vries, Timothy S., Aleksandrs Prokofjevs, Jeremy N. Harvey i Edwin Vedejs. "Superelectrophilic Intermediates in Nitrogen-Directed Aromatic Borylation". Journal of the American Chemical Society 131, nr 41 (21.10.2009): 14679–87. http://dx.doi.org/10.1021/ja905369n.
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Lv, Jiahang, Xiangyang Chen, Xiao-Song Xue, Binlin Zhao, Yong Liang, Minyan Wang, Liqun Jin i in. "Metal-free directed sp2-C–H borylation". Nature 575, nr 7782 (30.09.2019): 336–40. http://dx.doi.org/10.1038/s41586-019-1640-2.
Pełny tekst źródłaRozprawy doktorskie na temat "Directed borylation"
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Crossley, Daniel. "Directed C-H borylation for the synthesis of fused and ladder type conjugated oligomers and polymers". Thesis, University of Manchester, 2016. https://www.research.manchester.ac.uk/portal/en/theses/directed-ch-borylation-for-the-synthesis-of-fused-and-ladder-type-conjugated-oligomers-and-polymers(8c96a89b-7442-41f3-839b-56148b5fd458).html.
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The synthesis, photophysical and electronic properties of a series of novel boron containing fused and ladder type donor-acceptor (D-A) oligomers and polymers are reported. The synthesis was achieved through coordination of the basic functionality of the ubiquitous benzothiadiazole acceptor unit onto a boron Lewis acid followed by an electrophilic aromatic borylation resulting in the formation of fused and ladder type structures (termed borylative fusion). The novel C,N-chelated borane structures disclosed herein are a new member of a large family of tetra-coordinate organoboron compounds that are used for the construction of highly emissive materials. Upon borylation large bathochromic shifts in the absorption and fluorescence spectra were observed, DFT and cyclic voltammetry demonstrate that this is a result of a significant reduction of the LUMO energy levels whist the HOMO energy levels remains relatively unperturbed. These large bathochromic shifts lead to materials that show far red/NIR emission in the solid state with absolute quantum yields of up to 44%. Furthermore, the frontier molecular orbital energy levels of these fused structures can be modulated through judicious selection of the exocyclic boron substituents. These novel borocycles also proved stable to a range of cross-coupling conditions which facilitated further modulation of the frontier molecular orbitals and emissive properties. Borylative fusion was also applicable to D-A conjugated polymers, this represents a facile post-polymerisation functionalisation that is an effective method of modulating the photophysical properties of D-A conjugated polymers. Solution processed OLEDs with far red/NIR electroluminescence (EL) were fabricated from these materials. These devices showed good external quantum efficiency values (EQE) for the far red/NIR region of the electromagnetic spectrum (EQE > 0.4 % for maximum EL > 700 nm).
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Del, Grosso Alessandro. "Borenium cations for the direct electrophilic borylation of arenes". Thesis, University of Manchester, 2013. https://www.research.manchester.ac.uk/portal/en/theses/borenium-cations-for-the-direct-electrophilic-borylation-of-arenes(a505cdb2-08fe-43a0-ad0b-86ab357fadd1).html.
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A catalytic (in Brønsted superacid) and a stoichiometric process were developed to synthesise aryl boronic esters with boron cations via electrophilic arene borylation. The treatment of CatBX (Cat = catecholate; X = Cl, Br) with the triethyl salt [Et3Si][closo-CB11H6Br6] in arene solvent gave a transient boron electrophile that reacted as a synthetic equivalent of [CatB]+ in intermolecular electrophilic aromatic borylation at 25 °C. The by-product of the reaction was a strong Brønsted acid that was able to catalyse arene borylation using CatBH at high temperature. This catalytic process furnished aryl boronic esters in high yield with H2 as the only by-product. The use of the robust and weakly coordinating anion [closo-CB11H6Br6]- and the electrophile-resistant catecholborane were crucial for the catalytic process. The reaction mixture of R2BCl (R2 = Cat, Cl4Cat, Cl2), aprotic amine and AlCl3 mainly gave a borenium salt [R2B(amine)][AlCl4] which was in equilibrium with neutral species as revealed by NMR spectroscopy and reactivity studies. This reaction mixture was effective for the regioselective borylation, by electrophilic aromatic substitution, of a range of N-heterocycles, thiophenes and anilines at room temperature. The transterification in situ provided the synthetically useful and more stable pinacol boronate esters in excellent isolated yield. This process displayed remarkable functional-group tolerance for a boron based strong Lewis acid with weak bases (for example -NMe2), ether, and halogen groups all compatible. This process represents a new and inexpensive one-pot direct arene borylation methodology for producing pinacol boronate esters.
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Bentley, Sierra Kathleen. "Selective Direct Borylation and Late-Stage Functionalization of 1,2-Azaborines:". Thesis, Boston College, 2020. http://hdl.handle.net/2345/bc-ir:109014.
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Thesis advisor: Shih-Yuan LiuDescribed herein is the development of a method to directly borylate the C5-position of monocyclic 1,2-azaborines without the use of a metal catalyst, kinetic resolution or directing group. This method tolerates different substitution on the boron as well as at the C3-position of the azaborine. A new BN-isostere of the drug molecule, felbinac, was synthesized to demonstrate the application of this method
Thesis (MS) — Boston College, 2020
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry
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Coapes, Richard Benjamin. "Rhodium catalysed borylation reactions via direct and indirect C-H activation". Thesis, Durham University, 2002. http://etheses.dur.ac.uk/4176/.
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This thesis describes both direct and indirect C-H activation borylation processes, catalysed by several Rh-based catalyst precursors. Chapter One presents an overview of the processes investigated, namely diboration, dehydrogenative borylation, and direct C-H activation of hydrocarbon substrates, which give borylated species that are of interest to synthetic chemists. The uses of such borylated species are also highlighted. Chapter Two highlights the synthetic procedure for the synthesis of the catalyst precursor [Rh(acac)(C0E)(_2)], which can be used to prepare bis-phosphine catalyst precursors of the form [Rh(acacXP(_2))]- Although a procedure appears in the literature, it is not well cited. Also, this new procedure replaces [Tl(acac)] with [Na(acac)] and hence avoids the use of thallium salts. Chapter Three investigates the reaction of two vinyl(boronate) esters (VBEs) with Bzcat], and a wide array of catalyst precursors, which yield, among other species, the tris(boronate) esters ArCH(_2)C(Bcat)(_3) and ArCH(Bcat)CH(Bcat)(_3); the former results from the addition of both borons of the B(_2) unit to the same carbon atom, and are of interest due to their wide synthetic versatility. Chapter Four investigates the dehydrogenative borylation of alkenes using both HBpin and B2pin2, and several catalyst precursors. Most significantly, this route allows the synthesis of 1,1-disubstituted vinyl(boronate) esters that cannot be made by alkyne hydroboration. Chapter Five investigates the direct C-H activation of benzylic and aromatic hydrogens using the catalyst precursor [Rh(Cl)(N(_2))(P(^i)Pr(_3))(_2)]. This allows the functionalisation of hydrocarbon substrates, which are ubiquitous. Chapter Six investigates the stability of B-chlorocatecholborane to phosphines with the view to a boron analogue of the Heck reaction. In such a reaction, phosphmes would likely be employed on the catalyst. An understanding of the stability of the boron reagent under typical reaction conditions is needed, therefore, in order to prevent degradation of B-chlorocatecholborane, a process that is known for catecholborane.
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Eliseeva, Maria N. "New Route to a [5,5] Carbon Nanotube End-Cap via Direct Borylation of Corannulene". Thesis, Boston College, 2011. http://hdl.handle.net/2345/2752.
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Thesis advisor: Lawrence T. ScottThe Scott lab is interested in the functionalization of corannulene as a building block for large polycyclic aromatic hydrocarbons and carbon nanotube end-cap precursors. Toward that end, a new approach to the direct five-fold borylation of corannulene with iridium (I) catalysts via C-H activation has been explored. It has been discovered that the addition of catalytic amounts of base to the reaction mixture promotes the formation of symmetrical penta-borylated corannulene in a good yield on a sizable scale. All byproducts can be easily removed with iterative methanol washes. The present work also provides proof of the reversibility of the direct borylation reaction under the conditions used. Furthermore, modified Suzuki-Miyaura conditions have been employed to synthesize pentakis(2,6-dichlorophenyl)corannulene, a precursor for a [5,5] carbon nanotube end-cap. The reported reactions provide good yields and are scalable
Thesis (MS) — Boston College, 2011
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry
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Mori, Goro, Hiroshi Shinokubo i Atsuhiro Osuka. "Highly selective Ir-catalyzed direct sixfold borylation of peripheral aromatic substituents on hexakisaryl-substituted [28]hexaphyrin(1.1.1.1.1.1)". Elsevier, 2008. http://hdl.handle.net/2237/12313.
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Martin, Thibaut. "Etude de nouvelles méthodologies d'hétéroarylation directe de liaison C-Het C-Br en série thiazolique : application à la synthèse de coeurs thiazolylpyridiniques des thiopeptides de la série d". Phd thesis, INSA de Rouen, 2010. http://tel.archives-ouvertes.fr/tel-00577166.
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Face à l'apparition alarmante et continue de résistance massive des bactéries à l'arsenal actuel d'antibiotiques, la recherche de nouveaux agents antibactériens est actuellement un enjeu sociétal de tout premier ordre. Bien que connus depuis plus de 50 ans, les thiopeptides antibiotiques suscitent actuellement un très fort regain d'intérêt de la communauté scientifique internationale en raison de leurs propriétés antibactériennes remarquables, notamment contre les staphylococcus areus résistants à la méthiciline et les enterococci résistants à la vancomycine, impliquées dans de nombreuses infections qui engagent la vie des patients, et qui s'exercent de façon très intéressante selon deux modes d'action d'inhibition de la synthèse protéique originaux et encore inexploités en thérapie antibiotique humaine. Le travail développé s'inscrit dans ce programme international de valorisation pharmacologique qui repose pour une grande part sur le développement d'approches synthétiques rapides et modulables. Le projet a été centré en particulier sur la conception et la mise en oeuvre de nouveaux plans de synthèse des unités centrales di- ou trithiazolylpyridines, appelées coeurs hétérocycliques, communs à de nombreux thiopeptides de la série d et qui représentent les principaux défis synthétiques. Dans le cadre d'un programme de recherche du laboratoire ciblé sur l'étude de nouvelles méthodes de fonctionnalisation directe d'aromatiques et d'hétérocyclique, un premier travail méthodologique d'étude de la fonctionnalisation directe dans deux séries structurellement représentatives, thiazole-4-carboxylate et 2-cétothiazole, a été réalisé. Ainsi, une nouvelle méthodologie originale d'hétéroarylation directe pallado-catalysée régioselective du thiazole-4-carboxylate de tert-butyle avec une large gamme d'halogéno(hétéro)aromatiques a été développée avec succès. Une seconde méthodologie originale d'hétéroarylation directe de 4-bromo-2-cétothiazoles selon une séquence réactionnelle de boroylation pallado-catalysée suivie d'un couplage de Suzuki-Miyaura (BSC) a également été développée. Un second travail a porté sur l'exploitation des deux méthodologies de fonctionnalisation directe en série thiazolique développées et associées à la méthodologie de construction thiazolique de Hantzsch pour proposer et mettre en oeuvre un nouveau plan de synthèse expéditif et général d'accès aux coeurs hétérocycliques communs à une grande majorité des thiopeptides de la série d basé sur la fonctionnalisation séquencée d'un précurseur pyridinique aisément accessible. En particulier, la stratégie envisagée a permis, à partir des esters 5-bromopicolinates, la préparation tout d'abord d'un analogue thiazolique du coeur hétérocyclique des sulfomycines puis celle des coeurs hétérocycliques des micrococcines et des amithiamicynes.
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Lassalas, Pierrik. "Étude de nouvelles méthodologies d’arylation directe en séries azole et pyridine : Application à la synthèse de coeurs de thiopeptides antibiotiques de la série d". Thesis, Rouen, INSA, 2012. http://www.theses.fr/2012ISAM0024/document.
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Face à l’apparition grandissante de souches bactériennes multi-résistantes à l’arsenal d’antibiotiques actuels, les thiopeptides antibiotiques, bien que connus depuis plus de 60 ans, suscitent actuellement un fort regain d’intérêt. En effet, cette classe de molécules présente une forte activité antibiotique contre des souches bactériennes résistantes et multirésistantes, et met en œuvre deux modes d’inhibition originaux de la synthèse protéique encore inexploités en thérapie antibiotique humaine. Leur développement pharmacologique est en particulier freiné par la difficulté de préparation de ces molécules très complexes. L'élaboration d'une stratégie innovante de synthèse de la partie la plus complexe de ces molécules, le cœur hétérocyclique est étudiée dans ce travail. Cette approche repose sur l'étude et la valorisation de nouvelles méthodologies de fonctionnalisation directe des liaisons C-H et C-X de mono- et bis-thiazoles avec une large gamme d’hétéroaromatiques. Sa viabilité est démontrée par la préparation du cœur hétérocyclique commun aux amythiamicinesDue to the emergence of multiresistant bacterial strains to standard antibacterial treatments, thiopeptides antibiotics are actually highly considered, though they are known for 60 years. They show an excellent antibiotic activity against multiresistant bacterial strains, and implement two originals inhibition mechanisms of protein synthesis, still unemployed in human therapy. However, the difficulty to prepare these complex macromolecules limits their pharmacological development. The development of a new strategy to synthetize the most complicated part of these macromolecules, their heterocyclic core, is studied here in. This approach is based on the study and the exploitation of novel direct C-H and C-X transition-metal-catalyzed couplings of mono- and bithiazoles units with a broad panel of heteroaromatics. Its viability is here demonstrated trough the multi-step synthesis of the common heterocyclic core of amythiamicins
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Lassalas, Pierrik. "Étude de nouvelles méthodologies d'arylation directe en séries azole et pyridine : Application à la synthèse de coeurs de thiopeptides antibiotiques de la série d". Phd thesis, INSA de Rouen, 2012. http://tel.archives-ouvertes.fr/tel-00857574.
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Face à l'apparition grandissante de souches bactériennes multi-résistantes à l'arsenal d'antibiotiques actuels, les thiopeptides antibiotiques, bien que connus depuis plus de 60 ans, suscitent actuellement un fort regain d'intérêt. En effet, cette classe de molécules présente une forte activité antibiotique contre des souches bactériennes résistantes et multirésistantes, et met en œuvre deux modes d'inhibition originaux de la synthèse protéique encore inexploités en thérapie antibiotique humaine. Leur développement pharmacologique est en particulier freiné par la difficulté de préparation de ces molécules très complexes. L'élaboration d'une stratégie innovante de synthèse de la partie la plus complexe de ces molécules, le cœur hétérocyclique est étudiée dans ce travail. Cette approche repose sur l'étude et la valorisation de nouvelles méthodologies de fonctionnalisation directe des liaisons C-H et C-X de mono- et bis-thiazoles avec une large gamme d'hétéroaromatiques. Sa viabilité est démontrée par la préparation du cœur hétérocyclique commun aux amythiamicines.
Części książek na temat "Directed borylation"
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Yang, Y., i C. Wang. "2.15 Manganese-Catalyzed C—H Functionalization". W Base-Metal Catalysis 2. Stuttgart: Georg Thieme Verlag KG, 2023. http://dx.doi.org/10.1055/sos-sd-239-00231.
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AbstractManganese-catalyzed directed C—H functionalization is an efficient and straightforward approach for the formation of a variety of C—C and C—heteroatom bonds. In this review, we summarize the most significant advances in manganese-catalyzed C(sp2)—H functionalizations, including C—H alkenylation, alkylation, allylation, cyclization, amination, cyanation, borylation, and hydroxymethylation. The chapter is classified based on the type of newly formed chemical bond (C—C, C—N, C—B, and C—D bonds) and the reacting partner.
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Taber, Douglass. "Preparation of Benzene Derivatives". W Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0063.
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Several new methods have been put forward for the functionalization of benzene derivatives. J. S. Yadav of the Indian Institute of Chemical Technology, Hyderabad has devised (Chem. Lett. 2008, 37, 652) a procedure for direct thiocyanation, converting 1 into 2. Sukbok Chang of KAIST has established (Chem. Commun. 2008, 3052) that both NH4Cl and aqueous NH3 could be used to directly aminate an aryl iodide such as 3. John F. Hartwig of the University of Illinois has developed (J. Am. Chem. Soc. 2008, 130, 7534) a protocol for the directed borylation of anilines such as 5 and of phenols, based on a transient silylation. Karsten Menzel of Merck West Point (Tetrahedron Lett. 2008, 49, 415) has observed selective exchange of tribromobenzene derivatives such as 7, with the direction of the selectivity being controlled by the fourth substituent on the benzene. Gary A. Molander of the University of Pennsylvania has extensively developed the stable, readily prepared trifluoroborates, exemplified by 10 (J. Org. Chem. 2008, 73, 2052) and 14 (Organic Lett. 2008, 10, 1795) as partners for Suzuki-Miyaura coupling. The conversion of 9 to 10 is complementary to aminocarbonylation, exemplified by the conversion of 12 to 13 reported (Tetrahedron Lett. 2008, 49, 2221) by Bhalchandra M. Bhanage of the Institute of Chemical Technology, University of Mumbai. The coupling of 9 with 14 is complementary to the long-known Heck coupling of an aryl halide such as 16 with an allylic alcohol, as illustrated by the preparation of 18 described (Tetrahedron Lett. 2008, 49, 3279) by Martin E. Maier of the Universität Tübingen. Professor Hartwig has also (Organic Lett. 2008, 10, 1545, 1549) optimized conditions for the Pd-catalyzed arylation of ester enolates such as 19. Gang Zhou of Schering-Plough, Kenilworth, NJ has developed (Organic Lett. 2008, 10, 2517) a related transformation, the arylation of deprotonated sulfonamides. Peter Somfai of the Royal Institute of Technology, Stockholm has established (Angew. Chem. Int. Ed. 2008, 47, 1907) a complementary procedure, base-mediated elimination of t -butoxide from 24, followed by 1,2-addition of an aryl or heteroaryl Grignard reagent.
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Collier, S. J. "Direct Borylation of Imines (or Enamines)". W Ene-X Compounds (X=S, Se, Te, N, P), 1. Georg Thieme Verlag KG, 2007. http://dx.doi.org/10.1055/sos-sd-033-00571.
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Miyaura, N. "Direct Borylation of Alkanes and Arenes". W Boron Compounds, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-006-00223.
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Hall, D. G., i H. Zheng. "Synthesis by Direct Borylation with Borenium Cations". W Boron Compounds, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-106-00009.
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Taber, Douglass F. "Substituted Benzenes: The Gu Synthesis of Rhazinal". W Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0065.
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Sisir K. Mandal of Asian Paints R&T Centre, Mumbai used (Tetrahedron Lett. 2013, 54, 530) a Ru catalyst to couple 2 with an electron-rich arene 1 to give 3. Jun-ichi Yoshida of Kyoto University (J. Am. Chem. Soc. 2013, 135, 5000) and John F. Hartwig of the University of California, Berkeley (J. Am. Chem. Soc. 2013, 135, 8480) also reported direct amination protocols. Tommaso Marcelli of the Politecnico di Milano and Michael J. Ingleson of the University of Manchester effected (J. Am. Chem. Soc. 2013, 135, 474) the electrophilic borylation of the aniline 4 to give 5. The regioselectivity of Ir-catalyzed borylation (J. Am. Chem. Soc. 2013, 135, 7572; Org. Lett. 2013, 15, 140) is complementary to the electrophilic process. Professor Hartwig carried (Angew. Chem. Int. Ed. 2013, 52, 933) the borylated product from 6 onto Ni-mediated coupling to give the alkylated product 7. Weiping Su of the Fujian Institute of Research on the Structure of Matter devised (Org. Lett. 2013, 15, 1718) an intriguing Pd-mediated oxidative coupling of nitroethane 9 with 8 to give 10. The coupling is apparently not proceeding via nitroethylene. Peiming Gu of Ningxia University developed (Org. Lett. 2013, 15, 1124) an azide-based cleavage that converted the aldehyde 11 into the formamide 13. Zhong-Quan Liu of Lanzhou University showed (Tetrahedron Lett. 2013, 54, 3079) that an aromatic carboxylic acid 14 could be oxidatively decarboxylated to the chloride 15. Gérard Cahiez of the Université Paris 13 found (Adv. Synth. Catal. 2013, 355, 790) mild Cu-catalyzed conditions for the reductive decarboxylation of aromatic carboxylic acids, and Debabrata Maiti of the Indian Institute of Technology, Mumbai found (Chem. Commun. 2013, 49, 252) Pd-mediated conditions for the dehydroxymethylation of benzyl alcohols (neither illustrated). Pravin R. Likhar of the Indian Institute of Chemical Technology prepared (Adv. Synth. Catal. 2013, 355, 751) a Cu catalyst that effected Castro-Stephens coupling of 16 with 17 at room temperature. Arturo Orellana of York University (Chem. Commun. 2013, 49, 5420) and Patrick J. Walsh of the University of Pennsylvania (Org. Lett. 2013, 15, 2298) showed that a cyclopropanol 20 can couple with an aryl halide 19 to give 21.
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Taber, Douglass F. "C–H Functionalization". W Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0021.
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Konstantin P. Bryliakov of the Boreskov Institute of Catalysis devised (Org. Lett. 2012, 14, 4310) a manganese catalyst for the selective tertiary hydroxylation of 1 to give 2. Note that the electron-withdrawing Br deactivates the alternative methine H. Bhisma K. Patel of the Indian Institute of Technology, Guwahati selectively oxidized (Org. Lett. 2012, 14, 3982) a benzylic C–H of 3 to give the corresponding benzoate 4. Dalibor Sames of Columbia University cyclized (J. Org. Chem. 2012, 77, 6689) 5 to 6 by intramolecular hydride abstraction followed by recombination. Thomas Lectka of Johns Hopkins University showed (Angew. Chem. Int. Ed. 2012, 51, 10580) that direct C–H fluorination of 7 occurred predominantly at carbons 3 and 5. John T. Groves of Princeton University reported (Science 2012, 337, 1322) an alternative manganese porphyrin catalyst (not illustrated) for direct fluorination. C–H functionalization can also be mediated by a proximal functional group. John F. Hartwig of the University of California, Berkeley effected (J. Am. Chem. Soc. 2012, 134, 12422) Ir-mediated borylation of an ether 9 in the position β to the oxygen to give 10. Uttam K. Tambar of the UT Southwestern Medical Center devised (J. Am. Chem. Soc. 2012, 134, 18495) a protocol for the net enantioselective amination of 11 to give 12. Conversion of a C–H bond to a C–C bond can be carried out in an intramolecular or an intermolecular sense. Kilian Muñiz of the Catalan Institution for Research and Advanced Studies cyclized (J. Am. Chem. Soc. 2012, 134, 15505) the terminal alkene 13 directly to the cyclopentene 15. Olivier Baudoin of Université Claude Bernard Lyon 1 closed (Angew. Chem. Int. Ed. 2012, 51, 10399) the pyrrolidine ring of 17 by selective activation of a methyl C–H of 16. Jeremy A. May of the University of Houston found (J. Am. Chem. Soc. 2012, 134, 17877) that the Rh carbene derived from 18 inserted into the distal alkyne to give a new Rh carbene 19, which in turn inserted into a C–H bond adjacent to the ether oxygen to give 20.
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Taber, Douglass F. "Enantioselective Preparation of Alcohols and Amines". W Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0036.
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Renat Kadyrov of Evonik Degussa and Magnus Rueping of RWTH Aachen developed (Angew. Chem. Int. Ed. 2009, 49, 7556) an effective catalyst for the enantioselective hydrogenation of an α-hydroxy ketone 1 to the 1,2-diol 2 . Yong-Gui Zhou of the Dalian Institute of Chemical Physics showed (J. Org. Chem. 2009, 74, 5633) that a sultam such as 3 could be reduced with high ee to the sulfonamide 4. They also used this same approach to prepare both α-aryl and α,α-diaryl amines. David W. C. MacMillan of Princeton University described (Angew. Chem. Int. Ed. 2009, 49, 5121) the optimized enantioselective α-chlorination of an aldehyde 5 and the direct processing of the product to the epoxide 6. Erick M. Carreira of ETH Zürich reported (Synlett 2009, 2076) an alternative route to high ee epoxides by decarbonylation of an epoxy aldehyde 7. James P. Morken of Boston College established (J. Am. Chem. Soc. 2009, 131, 13210) a procedure for the enantioselective bis borylation of a terminal alkene 9, leading after oxidation to the 1,2-diol 10. Ben L. Feringa of the University of Groningen took advantage (J. Am. Chem. Soc. 2009, 131, 9473) of their alternative Wacker conditions to convert a primary allylic carbonate 11 to the protected β-amino aldehyde 12. Chao-Shan Da of Lanzhou University devised (Organic Lett. 2009, 11, 5578) additives that allow the direct enantioselective addition of a Grignard reagent 14 to an aldehyde. The enantioselective addition of substituted ketenes to aldehydes has long been established. Yun-Ming Lin of the University of Toledo developed (Synlett 2009, 1675) a catalyst system for the enantioselective addition of ketene 17 itself. An alkenyl silane 19 can readily be prepared from the corresponding terminal alkene (J. Org. Chem. 2010, 75, 1701). Koichi Mikami of the Tokyo Institute of Technology showed (J. Am. Chem. Soc. 2009, 131, 13922) that such alkenyl silanes add to ethyl glyoxylate 20 with high ee. Amir H. Hoveyda of Boston College devised (J. Am. Chem. Soc. 2009, 131, 18234) a procedure for the enantioselective conversion of a terminal alkyne 22 to the 1,2-bis boryl alkane, which he took on directly to the coupled product 24.
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Taber, Douglass F. "Enantioselective Synthesis of Alcohols and Amines: The Fujii/Ohno Synthesis of (+)-Lysergic Acid". W Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0035.
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Ramón Gómez Arrayás and Juan C. Carretero of the Universidad Autónoma de Madrid effected (Chem. Commun. 2011, 47, 6701) enantioselective conjugate borylation of an unsaturated sulfone 1, leading to the alcohol 2. Robert E. Gawley of the University of Arkansas found (J. Am. Chem. Soc. 2011, 133, 19680) conditions for enantioselective ketone reduction that were selective enough to distinguish between the ethyl and propyl groups of 3 to give 4. Vicente Gotor of the Universidad de Oviedo used (Angew. Chem. Int. Ed. 2011, 50, 8387) an overexpressed Baeyer-Villiger monoxygenase to prepare 6 by dynamic kinetic resolution of 5. Li Deng of Brandeis University prepared (J. Am. Chem. Soc. 2011, 133, 12458) 8 in high ee by kinetic enantioselective migration of the alkene of racemic 7. Bernhard Breit of the Freiburg Institute for Advanced Studies established (J. Am. Chem. Soc. 2011, 133, 20746) the oxygenated quaternary center of 10 by the addition of benzoic acid to the allene 9. Keith R. Fandrick of Boehringer Ingelheim constructed (J. Am. Chem. Soc. 2011, 133, 10332) the oxygenated quaternary center of 13 by enantioselective addition of the propargylic nucleophile 12 to 11. Yian Shi of Colorado State University devised (J. Am. Chem. Soc. 2011, 133, 12914) conditions for the enantioselective transamination of the α-keto ester 14 to the amine 15. Professor Deng added (Adv. Synth. Catal. 2011, 353, 3123) 18 to an enone 17 to give the protected amine 19. Song Ye of the Institute of Chemistry, Beijing effected (J. Am. Chem. Soc. 2011, 133, 15894) elimination/addition of an unsaturated acid chloride 20 to give the γ-amino acid derivative 22. Frank Glorius of the Universität Münster added (Angew. Chem. Int. Ed. 2011, 50, 1410) an aldehyde 23 to 24 to give the amide 25. Sentaro Okamoto of Kanagawa University designed (J. Org. Chem. 2011, 76, 6678) an organocatalyst for the enantioselective Steglich rearrangement of 26, creating the aminated quaternary center of 27. Most impressive of all was the report (Org. Lett. 2011, 13, 5460) by Hélène Lebel of the Université de Montréal of the direct enantioselective C–H amination of 28 to give 29.
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Taber, Douglass. "Synthesis of Substituted Benzenes: The Carter Synthesis of Siamenol". W Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0062.
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Tosylates are among the least expensive, but also among the least reactive toward Pd(0) oxidative addition, of aryl sulfonates. Jie Wu of Fudan University has now devised conditions (J. Org. Chem. 2007, 72, 9346) for the Pd-catalyzed coupling of aryl tosylates such as 1 with arene trifluoroborates. Kei Manabe of RIKEN has found (Organic Lett. 2007, 9, 5593) that an ortho OH activates an adjacent Cl for Pd-mediated coupling, allowing the conversion of 4 to 6 . Philippe Uriac and Pierre van de Weghe of the Université de Rennes I have developed (Organic Lett. 2007, 9, 3623) conditions for the catalytic acylation of aryl halides with alkenyl acetates such as 8. Multi-component coupling lends itself well to diversity-oriented synthesis. As illustrated by the combination of 10 with 11 and 12 to give 13 reported (Organic Lett. 2007, 9, 5589) by Michael F. Greaney of the University of Edinburgh, benzynes can do double addition with high regiocontrol. For other recent references to unsymmetrical double additions to arynes, see Angew.Chem. Int. Ed. 2007, 46, 5921; Chem. Commun. 2007, 2405; and J. Am. Chem. Soc. 2006, 128, 14042. C-H functionalization of arenes is of increasing importance. John F. Hartwig of the University of Illinois has described (Organic Lett. 2007, 9, 757; 761) improved conditions for Ir-catalyzed meta borylation, and conditions for further coupling of the initial borate 16 to give amines such as 17. Lei Liu and Qing-Xiang Guo of the University of Science and Technology, Hefei have found (Tetrahedron Lett. 2007, 48, 5449) that oxygen can be used as the stoichiometric oxidant in the Pd-catalyzed functionalization of H’s ortho to anilides. Two other research groups (J. Am. Chem. Soc. 2007, 129, 6066; Angew. Chem. Int. Ed. 2007, 46, 5554; J. Org. Chem. 2007, 72, 7720) reported advances in this area. In a close competition, Jin-Quan Yu, now at Scripps/La Jolla (J. Am. Chem. Soc. 2007, 129, 3510) and Olafs Daugulis of the University of Houston (J. Am. Chem. Soc. 2007, 129, 9879) both reported that a carboxyl group can activate an ortho H for direct functionalization.