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Journal articles on the topic 'C-C bond catalysis'

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Author: Grafiati

Published: 10 December 2022

Last updated: 29 January 2023

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1

Mejía, Esteban, and Ahmad A. Almasalma. "Recent Advances on Copper-Catalyzed C–C Bond Formation via C–H Functionalization." Synthesis 52, no. 18 (May 19, 2020): 2613–22. http://dx.doi.org/10.1055/s-0040-1707815.

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Reactions that form C–C bonds are at the heart of many important transformations, both in industry and in academia. From the myriad of catalytic approaches to achieve such transformations, those relying on C–H functionalization are gaining increasing interest due to their inherent sustainable nature. In this short review, we showcase the most recent advances in the field of C–C bond formation via C–H functionalization, but focusing only on those methodologies relying on copper catalysts. This coinage metal has gained increased popularity in recent years, not only because it is cheaper and more abundant than precious metals, but also thanks to its rich and versatile chemistry.1 Introduction2 Cross-Dehydrogenative Coupling under Thermal Conditions2.1 C(sp3)–C(sp3) Bond Formation2.2 C(sp3)–C(sp2) Bond Formation2.3 C(sp2)–C(sp2) Bond Formation2.4 C(sp3)–C(sp) Bond Formation3 Cross-Dehydrogenative Coupling under Photochemical Conditions3.1 C(sp3)–C(sp3) Bond Formation3.2 C(sp3)–C(sp2) and C(sp3)–C(sp) Bond Formation4 Conclusion and Perspective

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2

Ohtaka, Atsushi. "Recent Progress of Metal Nanoparticle Catalysts for C–C Bond Forming Reactions." Catalysts 11, no. 11 (October 21, 2021): 1266. http://dx.doi.org/10.3390/catal11111266.

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Over the past few decades, the use of transition metal nanoparticles (NPs) in catalysis has attracted much attention and their use in C–C bond forming reactions constitutes one of their most important applications. A huge variety of metal NPs, which have showed high catalytic activity for C–C bond forming reactions, have been developed up to now. Many kinds of stabilizers, such as inorganic materials, magnetically recoverable materials, porous materials, organic–inorganic composites, carbon materials, polymers, and surfactants have been utilized to develop metal NPs catalysts. This review classified and outlined the categories of metal NPs by the type of support.

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3

Sieber, Joshua D., and Toolika Agrawal. "Recent Developments in C–C Bond Formation Using Catalytic Reductive Coupling Strategies." Synthesis 52, no. 18 (May 25, 2020): 2623–38. http://dx.doi.org/10.1055/s-0040-1707128.

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Metal-catalyzed reductive coupling processes have emerged as a powerful methodology for the introduction of molecular complexity from simple starting materials. These methods allow for an orthogonal approach to that of redox-neutral strategies for the formation of C–C bonds by enabling cross-coupling of starting materials not applicable to redox-neutral chemistry. This short review summarizes the most recent developments in the area of metal-catalyzed reductive coupling utilizing catalyst turnover by a stoichiometric reductant that becomes incorporated in the final product.1 Introduction2 Ni Catalysis3 Cu Catalysis4 Ru, Rh, and Ir Catalysis4.1 Alkenes4.2 1,3-Dienes4.3 Allenes4.4 Alkynes4.5 Enynes5 Fe, Co, and Mn Catalysis6 Conclusion and Outlook

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4

Nagorny, Pavel, and Zhankui Sun. "New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation." Beilstein Journal of Organic Chemistry 12 (December 23, 2016): 2834–48. http://dx.doi.org/10.3762/bjoc.12.283.

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Hydrogen bond donor catalysis represents a rapidly growing subfield of organocatalysis. While traditional hydrogen bond donors containing N–H and O–H moieties have been effectively used for electrophile activation, activation based on other types of non-covalent interactions is less common. This mini review highlights recent progress in developing and exploring new organic catalysts for electrophile activation through the formation of C–H hydrogen bonds and C–X halogen bonds.

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5

Lu, Yen-Chu, and Julian G. West. "C–C Bond Fluorination via Manganese Catalysis." ACS Catalysis 11, no. 20 (October 4, 2021): 12721–28. http://dx.doi.org/10.1021/acscatal.1c03052.

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6

Lu, Yen-Chu, and Julian G. West. "C–C Bond Fluorination via Manganese Catalysis." ACS Catalysis 11, no. 20 (October 4, 2021): 12721–28. http://dx.doi.org/10.1021/acscatal.1c03052.

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7

Wang, Yi, Anan Liu, Dongge Ma, Shuhong Li, Chichong Lu, Tao Li, and Chuncheng Chen. "TiO2 Photocatalyzed C–H Bond Transformation for C–C Coupling Reactions." Catalysts 8, no. 9 (August 27, 2018): 355. http://dx.doi.org/10.3390/catal8090355.

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Fulfilling the direct inert C–H bond functionalization of raw materials that are earth-abundant and commercially available for the synthesis of diverse targeted organic compounds is very desirable and its implementation would mean a great reduction of the synthetic steps required for substrate prefunctionalization such as halogenation, borylation, and metalation. Successful C–H bond functionalization mainly resorts to homogeneous transition-metal catalysis, albeit sometimes suffering from poor catalyst reusability, nontrivial separation, and severe biotoxicity. TiO2 photocatalysis displays multifaceted advantages, such as strong oxidizing ability, high chemical stability and photostability, excellent reusability, and low biotoxicity. The chemical reactions started and delivered by TiO2 photocatalysts are well known to be widely used in photocatalytic water-splitting, organic pollutant degradation, and dye-sensitized solar cells. Recently, TiO2 photocatalysis has been demonstrated to possess the unanticipated ability to trigger the transformation of inert C–H bonds for C–C, C–N, C–O, and C–X bond formation under ultraviolet light, sunlight, and even visible-light irradiation at room temperature. A few important organic products, traditionally synthesized in harsh reaction conditions and with specially functionalized group substrates, are continuously reported to be realized by TiO2 photocatalysis with simple starting materials under very mild conditions. This prominent advantage—the capability of utilizing cheap and readily available compounds for highly selective synthesis without prefunctionalized reactants such as organic halides, boronates, silanes, etc.—is attributed to the overwhelmingly powerful photo-induced hole reactivity of TiO2 photocatalysis, which does not require an elevated reaction temperature as in conventional transition-metal catalysis. Such a reaction mechanism, under typically mild conditions, is apparently different from traditional transition-metal catalysis and beyond our insights into the driving forces that transform the C–H bond for C–C bond coupling reactions. This review gives a summary of the recent progress of TiO2 photocatalytic C–H bond activation for C–C coupling reactions and discusses some model examples, especially under visible-light irradiation.

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8

Singh, Keisham. "Recent Advances in C–H Bond Functionalization with Ruthenium-Based Catalysts." Catalysts 9, no. 2 (February 12, 2019): 173. http://dx.doi.org/10.3390/catal9020173.

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The past decades have witnessed rapid development in organic synthesis via catalysis, particularly the reactions through C–H bond functionalization. Transition metals such as Pd, Rh and Ru constitute a crucial catalyst in these C–H bond functionalization reactions. This process is highly attractive not only because it saves reaction time and reduces waste,but also, more importantly, it allows the reaction to be performed in a highly region specific manner. Indeed, several organic compounds could be readily accessed via C–H bond functionalization with transition metals. In the recent past, tremendous progress has been made on C–H bond functionalization via ruthenium catalysis, including less expensive but more stable ruthenium(II) catalysts. The ruthenium-catalysed C–H bond functionalization, viz. arylation, alkenylation, annulation, oxygenation, and halogenation involving C–C, C–O, C–N, and C–X bond forming reactions, has been described and presented in numerous reviews. This review discusses the recent development of C–H bond functionalization with various ruthenium-based catalysts. The first section of the review presents arylation reactions covering arylation directed by N–Heteroaryl groups, oxidative arylation, dehydrative arylation and arylation involving decarboxylative and sp3-C–H bond functionalization. Subsequently, the ruthenium-catalysed alkenylation, alkylation, allylation including oxidative alkenylation and meta-selective C–H bond alkylation has been presented. Finally, the oxidative annulation of various arenes with alkynes involving C–H/O–H or C–H/N–H bond cleavage reactions has been discussed.

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9

Marchese, Austin D., Bijan Mirabi, Colton E. Johnson, and Mark Lautens. "Reversible C–C bond formation using palladium catalysis." Nature Chemistry 14, no. 4 (March 17, 2022): 398–406. http://dx.doi.org/10.1038/s41557-022-00898-0.

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10

Ma, Dongge, Anan Liu, Shuhong Li, Chichong Lu, and Chuncheng Chen. "TiO2 photocatalysis for C–C bond formation." Catalysis Science & Technology 8, no. 8 (2018): 2030–45. http://dx.doi.org/10.1039/c7cy01458a.

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11

Simon, Marc-Olivier, Gaël Ung, and Sylvain Darses. "Tandem Catalysis: Alcohol Oxidation and CC Bond Formation via CH Bond Activation." Advanced Synthesis & Catalysis 353, no. 7 (April 28, 2011): 1045–48. http://dx.doi.org/10.1002/adsc.201000884.

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12

Böhm, Volker P. W., Christian W. K. Gstöttmayr, Thomas Weskamp, and Wolfgang A. Herrmann. "Catalytic C−C Bond Formation through Selective Activation of C−F Bonds." Angewandte Chemie International Edition 40, no. 18 (September 17, 2001): 3387–89. http://dx.doi.org/10.1002/1521-3773(20010917)40:18<3387::aid-anie3387>3.0.co;2-6.

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13

Jacobsen, Eric N., Andreas Pfaltz, and Masakatsu Shibasaki. "Catalytic CC Bond Formation." Advanced Synthesis & Catalysis 347, no. 11-13 (October 2005): 1471. http://dx.doi.org/10.1002/adsc.200505313.

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14

Li, Qiuyun, Xin Yuan, Bin Li, and Baiquan Wang. "The regioselective annulation of alkylidenecyclopropanes by Rh(iii)-catalyzed C–H/C–C activation to access spirocyclic benzosultams." Chemical Communications 56, no. 12 (2020): 1835–38. http://dx.doi.org/10.1039/c9cc09621c.

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The synthesis of spirocyclic benzosultams from N-sulfonyl ketimine and alkylidenecyclopropanes under Rh(iii) catalysis has been developed. This transformation enables the formation of two C–C bonds and a double bond with high E-selectivity.

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15

Horino, Yoshikazu. "Rhenium-Catalyzed CH and CC Bond Activation." Angewandte Chemie International Edition 46, no. 13 (March 19, 2007): 2144–46. http://dx.doi.org/10.1002/anie.200605228.

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16

Lapshin, Ivan V., Alexander A. Kissel, and Alexander A. Trifonov. "Complexes of Rare- and Alkaline-Earth Elements in Catalytic Intermolecular Hydrophosphination of Multiple C—C Bonds." Vestnik RFFI, no. 2 (June 25, 2019): 58–73. http://dx.doi.org/10.22204/2410-4639-2019-102-02-58-73.

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In accordance with United Nations General Assembly resolution, the year 2019 was proclaimed the International Year of the Periodic Table of Chemical Elements. Rare-earth elements were discovered during the time of the Periodic System development. In the past few decades, their compounds have attracted great interest due to their unique reactivity. This review covers recent achievements in the field of intermolecular hydrophosphination of alkenes, dienes and alkynes, which is catalyzed by rare earth and alkaline-earth metal complexes. Catalytic hydrophosphination reaction is the addition of an P—H bond to С—С multiple bonds, and offers an efficient and elegant synthetic approach to production of the organophosphorus compounds widely used in industrial synthesis, pharmaceuticals, agrochemistry, and other areas. The high values of the ionic radii of rare earth and alkaline-earth metals in combination with the Lewis acidity provide their compounds with a pronounced tendency to complex formation and, accordingly, high coordination numbers. Due to high reactivity of M—E (E = C, H, N, P) bonds, ease of Ln—P ı-bond metathesis and multiple C—C bond insertions, these compounds offer new prospects for the catalysis of the alkenes and alkynes hydrophosphination. Therefore, complexes of non-toxic and relatively abundant in nature rare earth and alkaline earth metals can be a cheaper and more effective alternative to compounds of late transition metals in the catalysis of the C—P bond formation.

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17

Martinez, Rémi, Reynald Chevalier, Sylvain Darses, and Jean-Pierre Genet. "A Versatile Ruthenium Catalyst for CC Bond Formation by CH Bond Activation." Angewandte Chemie International Edition 45, no. 48 (December 11, 2006): 8232–35. http://dx.doi.org/10.1002/anie.200603786.

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18

Zhang, Dongju, Ruoxi Wang, and Rongxiu Zhu. "A New Pathway for Activation of C - C and C - H Bonds by Transition Metals in the Gas Phase." Australian Journal of Chemistry 58, no. 2 (2005): 82. http://dx.doi.org/10.1071/ch04154.

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C–H and C–C bond activation of hydrocarbons at metal centres are of fundamental importance in biochemistry, organometallic chemistry, and catalysis. The present work aims to search for novel mechanisms for activation of C–C and C–H bonds by transition metals in the gas phase. Using high-level density functional calculations, we systemically studied the reactions of Ti+, V+, and Fe+ with ethane, and proposed new pathways of C–C and C–H bond activation—concerted activation of C–C and C–H bonds, and 1,2-H2 elimination. These two pathways clearly differ from the general addition–elimination mechanism.

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19

Kim, Dong-Su, Woo-Jin Park, and Chul-Ho Jun. "Metal–Organic Cooperative Catalysis in C–H and C–C Bond Activation." Chemical Reviews 117, no. 13 (January 6, 2017): 8977–9015. http://dx.doi.org/10.1021/acs.chemrev.6b00554.

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20

Hiemstra, Henk, Floris P. Rutjes, Sape S. Kinderman, Jan H. van Maarseveen, and Hans E. Schoemaker. "C-C Bond Formation viaN-Phosphoryliminium Ions." Synthesis 2004, no. 09 (2004): 1413–18. http://dx.doi.org/10.1055/s-2004-822376.

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21

Gao, Han, Lingfei Hu, Yanlei Hu, Xiangying Lv, Yan-Bo Wu, and Gang Lu. "Origins of Lewis acid acceleration in nickel-catalysed C–H, C–C and C–O bond cleavage." Catalysis Science & Technology 11, no. 13 (2021): 4417–28. http://dx.doi.org/10.1039/d1cy00660f.

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22

Simon, Marc-Olivier, Gael Ung, and Sylvain Darses. "ChemInform Abstract: Tandem Catalysis: Alcohol Oxidation and C-C Bond Formation via C-H Bond Activation." ChemInform 42, no. 39 (September 1, 2011): no. http://dx.doi.org/10.1002/chin.201139167.

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23

Gao, Jian, Jie Feng, and Ding Du. "Shining Light on C−S Bonds: Recent Advances in C−C Bond Formation Reactions via C−S Bond Cleavage under Photoredox Catalysis." Chemistry – An Asian Journal 15, no. 22 (October 14, 2020): 3637–59. http://dx.doi.org/10.1002/asia.202000905.

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24

Giese, Bernd, and Tom Witzel. "Synthesis of“C-Disaccharides” by Radical CC Bond Formation." Angewandte Chemie International Edition in English 25, no. 5 (May 1986): 450–51. http://dx.doi.org/10.1002/anie.198604501.

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25

Yang, Qiaoyu, Xiaoxian Guo, Yuwan Liu, and Huifeng Jiang. "Biocatalytic C-C Bond Formation for One Carbon Resource Utilization." International Journal of Molecular Sciences 22, no. 4 (February 14, 2021): 1890. http://dx.doi.org/10.3390/ijms22041890.

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The carbon-carbon bond formation has always been one of the most important reactions in C1 resource utilization. Compared to traditional organic synthesis methods, biocatalytic C-C bond formation offers a green and potent alternative for C1 transformation. In recent years, with the development of synthetic biology, more and more carboxylases and C-C ligases have been mined and designed for the C1 transformation in vitro and C1 assimilation in vivo. This article presents an overview of C-C bond formation in biocatalytic C1 resource utilization is first provided. Sets of newly mined and designed carboxylases and ligases capable of catalyzing C-C bond formation for the transformation of CO2, formaldehyde, CO, and formate are then reviewed, and their catalytic mechanisms are discussed. Finally, the current advances and the future perspectives for the development of catalysts for C1 resource utilization are provided.

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26

Yang, Hai-Bin, and Dan-Hong Wan. "C–C Bond Acylation of Oxime Ethers via NHC Catalysis." Organic Letters 23, no. 3 (January 12, 2021): 1049–53. http://dx.doi.org/10.1021/acs.orglett.0c04248.

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27

McLean, Euan B., Vincent Gauchot, Sebastian Brunen, David J. Burns, and Ai-Lan Lee. "Dual copper- and photoredox-catalysed C(sp2)–C(sp3) coupling." Chemical Communications 55, no. 29 (2019): 4238–41. http://dx.doi.org/10.1039/c9cc01718f.

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The use of copper catalysis with visible light photoredox catalysis in a cooperative fashion has recently emerged as a versatile means of developing new C–C bond forming reactions. In this work, dual copper and photoredox catalysis is exploited to effect C(sp²)–C(sp³) cross-couplings between aryl boronic acids and benzyl bromides.

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28

Takahashi, Tamotsu, Zhiyi Song, Yi-Fang Hsieh, Kiyohiko Nakajima, and Ken-ichiro Kanno. "Once Cleaved C−C Bond Was Reformed: Reversible C−C Bond Cleavage of Dihydroindenyltitanium Complexes." Journal of the American Chemical Society 130, no. 46 (November 19, 2008): 15236–37. http://dx.doi.org/10.1021/ja805352z.

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29

Robertson, Katherine N., Osvald Knop, and T. Stanley Cameron. "C-H···H-C interactions in organoammonium tetraphenylborates: another look at dihydrogen bonds." Canadian Journal of Chemistry 81, no. 6 (June 1, 2003): 727–43. http://dx.doi.org/10.1139/v03-080.

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The crystal structures of the tetraphenylborates of the dabcoH+, guanidinium (MeCN solvate), and biguanidinium cations are shown to contain a variety of C-H···H-C dihydrogen (DB) bonds of nominally zero polarity, as well as a variety of N-H···N, C-H···N, N-H···Ph, and C-H···Ph hydrogen (HB) bonds. These intermolecular bonds have been characterized topologically after multipole refinement of the structures. The coexistence of the DBs and HBs in each of the structures makes it possible to establish their relative strength hierarchy. It also illustrates the importance of the DBs in satisfying the tendency of these structures to maximize the total intermolecular bonding engagement. To compare the above DBs with other DBs, the results of an extensive set of MP2/6-31G(d,p) calculations (supplied by I. Alkorta) were analyzed for reference correlations between the bond-critical parameters. Thus, for an X-H···H-Y bond, the difference Δε(H)m between the Mulliken charges on the H atoms in the uncomplexed X-H and H-Y components correlates quite well with the X-H···H-Y parameters and can be used for predicting the topological strength of an X-H···H-Y bond. The use of the difference Δε(H)c in the bond does not appear to change the correlation significantly; closer correlations are observed when the amount of charge transferred on formation of the H···H bond is used instead of Δε(H)m or Δε(H)c. Bonding interactions are obtained even between like or symmetry-related H atoms as a consequence of induced-dipole interactions, which accounts for the existence of the above intermolecular C-H···H-C bonds with d(H···H) = 2.182.57 Å, electron density at the bond-critical point of ~0.050.08 e/Å3, and a rough estimate of the H···H binding energy of ~1-5 kcal/mol. Examination of the bond-critical parameters of X-H···H-Y bonds also suggests a criterion of stability of these bonds with respect to the transition from non-shared (closed-shell) X-H···H-Y interaction to covalent (shared-shell) X···H-H···Y interaction. This transition appears to be discontinuous.Key words: bond-critical parameters, bond topology, dihydrogen bonds, hydrogen bonds, organoammonium tetraphenylborates.

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30

Schörgenhumer, Johannes, Maximilian Tiffner, and Mario Waser. "Chiral phase-transfer catalysis in the asymmetric α-heterofunctionalization of prochiral nucleophiles." Beilstein Journal of Organic Chemistry 13 (August 22, 2017): 1753–69. http://dx.doi.org/10.3762/bjoc.13.170.

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Chiral phase-transfer catalysis is one of the major catalytic principles in asymmetric catalysis. A broad variety of different catalysts and their use for challenging applications have been reported over the last decades. Besides asymmetric C–C bond forming reactions the use of chiral phase-transfer catalysts for enantioselective α-heterofunctionalization reactions of prochiral nucleophiles became one of the most important field of application of this catalytic principle. Based on several highly spectacular recent reports, we thus wish to discuss some of the most important achievements in this field within the context of this review.

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31

Shaaban, Saad, and Nuno Maulide. "Metal-Free Redox Transformations for C–C and C–N Bond Construction." Synlett 28, no. 20 (April 11, 2017): 2707–13. http://dx.doi.org/10.1055/s-0036-1588776.

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In this Account, the authors retrace their development of remote functionalisation reactions relying on photoredox catalysis. Inextricably connected to this is their discovery of small molecule organocatalysts that behave as formal reductive activators of diazonium salts, while requiring no promotion by visible light. This ultimately paved the way for the development of an unusual class of reactions in which the catalyst is also the nucleophile.

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32

Li, Lili, Wenbin Huang, Lijin Chen, Jiaxing Dong, Xuebing Ma, and Yungui Peng. "Silver-Catalyzed Oxidative C(sp3 )−P Bond Formation through C−C and P−H Bond Cleavage." Angewandte Chemie International Edition 56, no. 35 (July 21, 2017): 10539–44. http://dx.doi.org/10.1002/anie.201704910.

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33

Christoffers, Jens, Thomas Werner, and Michael Rössle. "Cerium-catalyzed oxidative C–C bond forming reactions." Catalysis Today 121, no. 1-2 (March 2007): 22–26. http://dx.doi.org/10.1016/j.cattod.2006.11.008.

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34

Hashmi, A. Stephen K., Lothar Schwarz, Ji-Hyun Choi, and Tanja M. Frost. "A New Gold-Catalyzed C−C Bond Formation." Angewandte Chemie International Edition 39, no. 13 (July 3, 2000): 2285–88. http://dx.doi.org/10.1002/1521-3773(20000703)39:13<2285::aid-anie2285>3.0.co;2-f.

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35

Winter, Christian, and Norbert Krause. "Rhodium(I)-Catalyzed Enantioselective CC Bond Activation." Angewandte Chemie International Edition 48, no. 14 (March 23, 2009): 2460–62. http://dx.doi.org/10.1002/anie.200805578.

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36

Averin, Alexei D., Anton S. Abel, Olga K. Grigorova, Gennadij V. Latyshev, Yury N. Kotovshchikov, Alexander Yu Mitrofanov, Alla Bessmertnykh-Lemeune, and Irina P. Beletskaya. "Recent achievements in copper catalysis for C–N bond formation." Pure and Applied Chemistry 92, no. 8 (September 25, 2020): 1181–99. http://dx.doi.org/10.1515/pac-2020-0301.

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AbstractA mini-review describes the development of the catalysis by Cu(I) complexes aimed at the formation of C–N bond at the Lomonosov MSU during 2010s. The main approach employs the amination of aryl and heteroaryl halides with the amines and polyamines, in this direction a great versatility of starting compounds was achieved: adamantane-containing amines, linear diamines, oxadiamines and polyamines, various aryl iodides and bromides, derivatives of pyridine, and quinoline were used for this purpose. In more peculiar cases, the copper catalysis was used for steroids transformations, including vinylation of azoles, wide-spread “click” reactions for the conjugate syntheses, and successful heterogenezation of the copper catalysts were also undertaken.

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37

Nebra, Noel. "High-Valent NiIII and NiIV Species Relevant to C–C and C–Heteroatom Cross-Coupling Reactions: State of the Art." Molecules 25, no. 5 (March 4, 2020): 1141. http://dx.doi.org/10.3390/molecules25051141.

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Ni catalysis constitutes an active research arena with notable applications in diverse fields. By analogy with its parent element palladium, Ni catalysts provide an appealing entry to build molecular complexity via cross-coupling reactions. While Pd catalysts typically involve a M0/MII redox scenario, in the case of Ni congeners the mechanistic elucidation becomes more challenging due to their innate properties (like enhanced reactivity, propensity to undergo single electron transformations vs. 2e− redox sequences or weaker M–Ligand interaction). In recent years, mechanistic studies have demonstrated the participation of high-valent NiIII and NiIV species in a plethora of cross-coupling events, thus accessing novel synthetic schemes and unprecedented transformations. This comprehensive review collects the main contributions effected within this topic, and focuses on the key role of isolated and/or spectroscopically identified NiIII and NiIV complexes. Amongst other transformations, the resulting NiIII and NiIV compounds have efficiently accomplished: i) C–C and C–heteroatom bond formation; ii) C–H bond functionalization; and iii) N–N and C–N cyclizative couplings to forge heterocycles.

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38

Kumagai, Naoya, and Masakatsu Shibasaki. "7-Azaindoline Auxiliary: A Versatile Attachment Facilitating Enantioselective C–C Bond-Forming Catalysis." Synthesis 51, no. 01 (November 30, 2018): 185–93. http://dx.doi.org/10.1055/s-0037-1610412.

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This short review provides an overview of 7-azaindoline auxiliaries in asymmetric catalysis. 7-Azaindoline serves as a useful attachment to carboxylic acids, and the thus-formed 7-azaindoline amides are amenable to atom-economical C–C bond-forming reactions with high stereoselectivity. The attachment is used for the sake of gaining traction in promoting the reaction of interest and can be easily removed after enantioselective reactions. Both nucleophilic and electrophilic catalyses are realized with broad tolerance for functional groups, showcasing the usefulness of 7-azaindoline auxiliaries for practical and streamlined synthesis of a wide range of acyclic chiral building blocks.1 Introduction2 7-Azaindoline as a Key Auxiliary3 7-Azaindoline Amide as a Pronucleophile3.1 α-Carbon-Substituted 7-Azaindoline Amide3.2 α-Nitrogen-Substituted 7-Azaindoline Amide3.3 α-Oxygen-Substituted 7-Azaindoline Amide3.4 α-Fluorocarbon-Substituted 7-Azaindoline Amide3.5 α-Halogen-Substituted 7-Azaindoline Amide3.6 α-Sulfur-Substituted 7-Azaindoline Amide4 7-Azaindoline Amide as an Electrophile4.1 Conjugate Addition of Butenolides4.2 1,3-Dipolar Cycloaddition of Nitrones5 Transformation of 7-Azaindoline Amide6 Conclusion

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Li, Jing-Yuan, Qing-Wen Song, Kan Zhang, and Ping Liu. "Catalytic Conversion of Carbon Dioxide through C-N Bond Formation." Molecules 24, no. 1 (January 5, 2019): 182. http://dx.doi.org/10.3390/molecules24010182.

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From the viewpoint of green chemistry and sustainable development, it is of great significance to synthesize chemicals from CO2 as C1 source through C-N bond formation. During the past several decade years, many studies on C-N bond formation reaction were involved, and many efforts have been made on the theory. Nevertheless, several great challenges such as thermodynamic limitation, low catalytic efficiency and selectivity, and high pressure etc. are still suffered. Herein, recent advances are highlighted on the development of catalytic methods for chemical fixation of CO2 to various chemicals through C-N bond formation. Meanwhile, the catalytic systems (metal and metal-free catalysis), strategies and catalytic mechanism are summarized and discussed in detail. Besides, this review also covers some novel synthetic strategies to urethanes based on amines and CO2. Finally, the regulatory strategies on functionalization of CO2 for N-methylation/N-formylation of amines with phenylsilane and heterogeneous catalysis N-methylation of amines with CO2 and H2 are emphasized.

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Uygur, Mustafa, Tobias Danelzik, and Olga García Mancheño. "Metal-free desilylative C–C bond formation by visible-light photoredox catalysis." Chemical Communications 55, no. 20 (2019): 2980–83. http://dx.doi.org/10.1039/c8cc10239b.

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Heilmann, Andreas, Jamie Hicks, Petra Vasko, Jose M. Goicoechea, and Simon Aldridge. "Carbon Monoxide Activation by a Molecular Aluminium Imide: C−O Bond Cleavage and C−C Bond Formation." Angewandte Chemie International Edition 59, no. 12 (February 18, 2020): 4897–901. http://dx.doi.org/10.1002/anie.201916073.

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Tang, Conghui, and Ning Jiao. "Copper-Catalyzed Aerobic Oxidative CC Bond Cleavage for CN Bond Formation: From Ketones to Amides." Angewandte Chemie International Edition 53, no. 25 (May 14, 2014): 6528–32. http://dx.doi.org/10.1002/anie.201403528.

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Lepitre, T., C. Pintiala, K. Muru, S. Comesse, A. Rebbaa, A. M. Lawson, and A. Daïch. "Competitive intramolecular C–C vs. C–O bond coupling reactions toward C6 ring-fused 2-pyridone synthesis." Organic & Biomolecular Chemistry 14, no. 14 (2016): 3564–73. http://dx.doi.org/10.1039/c6ob00303f.

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Doster, Meghan E., Jillian A. Hatnean, Tamara Jeftic, Sunjay Modi, and Samuel A. Johnson. "Catalytic C−H Bond Stannylation: A New Regioselective Pathway to C−Sn Bonds via C−H Bond Functionalization." Journal of the American Chemical Society 132, no. 34 (September 2010): 11923–25. http://dx.doi.org/10.1021/ja105588v.

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Li, Zhiping, Rong Yu, and Haijun Li. "Iron-Catalyzed CC Bond Formation by Direct Functionalization of CH Bonds Adjacent to Heteroatoms." Angewandte Chemie International Edition 47, no. 39 (September 15, 2008): 7497–500. http://dx.doi.org/10.1002/anie.200802215.

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Wang, Youliang, and Raymond A. Poirier. "Generalized valence bond study of rotational singlet structures and pi bond energies for systems containing C==C, Si==Si, and C==Si double bonds." Canadian Journal of Chemistry 76, no. 4 (April 1, 1998): 477–82. http://dx.doi.org/10.1139/v98-041.

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Ab initio GVB(6/12)/6-31G** calculations were performed on A2X==YB2 (A, B = H, F; X, Y = C, Si) to obtain the optimized geometries for planar and twisted singlet structures, and to also calculate pi bond energies (rotational barriers). The nature of C-C, Si-Si, and C-Si pi bonds has been investigated. The results show that the C-C pi bond energy (E pi (ethene) = 65.4 kcal/mol) decreases with increasing fluorine substitution. The pyramidalization at the carbon or silicon center for the twisted structures decreases the pi bond energies in the substituted ethenes and their silicon counterparts. The Si-Si (E pi (disilene) = 23.2 kcal/mol) and C-Si (E pi (silaethene) = 31.6 kcal/mol) pi bonds become much weaker. Fluorine substitution stabilizes both the diradical and the dipolar twisted singlet structures.Key words: pi bond energy, ab initio calculations, generalized valence bond, fluorine substitution, disilene, and silaethene.

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Ma, Dongge, Yi Wang, Anan Liu, Shuhong Li, Chichong Lu, and Chuncheng Chen. "Covalent Organic Frameworks: Promising Materials as Heterogeneous Catalysts for C-C Bond Formations." Catalysts 8, no. 9 (September 19, 2018): 404. http://dx.doi.org/10.3390/catal8090404.

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Covalent organic frameworks (COFs) are defined as highly porous and crystalline polymers, constructed and connected via covalent bonds, extending in two- or three-dimension. Compared with other porous materials such as zeolite and active carbon, the versatile and alternative constituent elements, chemical bonding types and characteristics of ordered skeleton and pore, enable the rising large family of COFs more available to diverse applications including gas separation and storage, optoelectronics, proton conduction, energy storage and in particular, catalysis. As the representative candidate of next-generation catalysis materials, because of their large surface area, accessible and size-tunable open nano-pores, COFs materials are suitable for incorporating external useful active ingredients such as ligands, complexes, even metal nanoparticles deposition and substrate diffusion. These advantages make it capable to catalyze a variety of useful organic reactions such as important C-C bond formations. By appropriate pore-engineering in COFs materials, even enantioselective asymmetric C-C bond formations could be realized with excellent yield and ee value in much shorter reaction time compared with their monomer and oligomer analogues. This review will mainly introduce and discuss the paragon examples of COFs materials for application in C-C bond formation reactions for the organic synthetic purpose.

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Ackerman, Laura K. G., Jesus I. Martinez Alvarado, and Abigail G. Doyle. "Direct C–C Bond Formation from Alkanes Using Ni-Photoredox Catalysis." Journal of the American Chemical Society 140, no. 43 (October 11, 2018): 14059–63. http://dx.doi.org/10.1021/jacs.8b09191.

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Jun, Chul-Ho, and Jung-Woo Park. "ChemInform Abstract: Metal-Organic Cooperative Catalysis in C-C Bond Activation." ChemInform 46, no. 47 (November 2015): no. http://dx.doi.org/10.1002/chin.201547248.

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PETERSEN, M., M. T. ZANNETTI, and W. D. FESSNER. "ChemInform Abstract: Tandem Asymmetric C-C Bond Formations by Enzyme Catalysis." ChemInform 28, no. 28 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199728223.

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