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Journal articles on the topic 'Carbon-heteroatom Bond Forming Reactions'

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Published: 6 September 2023

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1

Corma, A., A. Leyva-Pérez, and Maria J. Sabater. "Gold-Catalyzed Carbon−Heteroatom Bond-Forming Reactions." Chemical Reviews 111, no. 3 (2011): 1657–712. http://dx.doi.org/10.1021/cr100414u.

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2

Lumb, Jean-Philip, and Kenneth Esguerra. "Cu(III)-Mediated Aerobic Oxidations." Synthesis 51, no. 02 (2018): 334–58. http://dx.doi.org/10.1055/s-0037-1609635.

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CuIII species have been invoked in many copper-catalyzed transformations including cross-coupling reactions and oxidation reactions. In this review, we will discuss seminal discoveries that have advanced our understanding of the CuI/CuIII redox cycle in the context of C–C and C–heteroatom aerobic cross-coupling reactions, as well as C–H oxidation reactions mediated by CuIII–dioxygen adducts.1 General Introduction2 Early Examples of CuIII Complexes3 Aerobic CuIII-Mediated Carbon–Heteroatom Bond-Forming Reactions4 Aerobic CuIII-Mediated Carbon–Carbon Bond-Forming Reactions5 Bioinorganic Studies

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3

Takemoto, Yoshiji, and Hideto Miyabe. "ChemInform Abstract: Asymmetric Carbon-Heteroatom Bond-Forming Reactions." ChemInform 42, no. 18 (2011): no. http://dx.doi.org/10.1002/chin.201118241.

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4

Daoust, Benoit, Nicolas Gilbert, Paméla Casault, François Ladouceur, and Simon Ricard. "1,2-Dihaloalkenes in Metal-Catalyzed Reactions." Synthesis 50, no. 16 (2018): 3087–113. http://dx.doi.org/10.1055/s-0037-1610174.

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1,2-Dihaloalkenes readily undergo simultaneous or sequential difunctionalization through transition-metal-catalyzed reactions, which makes them attractive building blocks for complex unsaturated motifs. This review summarizes recent applications of such transformations in C–C and C–heteroatom bond forming processes. The facile synthesis of stereodefined alkene derivatives, as well as aromatic and heteroatomic compounds, from 1,2-dihaloalkenes is thus outlined.1 Introduction2 Synthesis of 1,2-Dihaloalkenes3 C–C Bond Forming Reactions4 C–Heteroatom Bond Forming Reactions5 Conclusion

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5

Miyabe, Hideto, and Yoshiji Takemoto. "Cascade radical reactions via carbon-carbon/heteroatom bond-forming process." Universal Organic Chemistry 2, no. 1 (2014): 1. http://dx.doi.org/10.7243/2053-7670-2-1.

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6

Hosoya, Keisuke, Minami Odagi, and Kazuo Nagasawa. "Guanidine organocatalysis for enantioselective carbon-heteroatom bond-forming reactions." Tetrahedron Letters 59, no. 8 (2018): 687–96. http://dx.doi.org/10.1016/j.tetlet.2017.12.058.

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7

Corma, A., A. Leyva-Perez, and Maria J. Sabater. "ChemInform Abstract: Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions." ChemInform 42, no. 29 (2011): no. http://dx.doi.org/10.1002/chin.201129225.

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8

Banerjee, Bubun. "Microwave-assisted Carbon-carbon and Carbon-heteroatom Bond Forming Reactions - Part 1A." Current Microwave Chemistry 7, no. 1 (2020): 3–4. http://dx.doi.org/10.2174/221333560701200422091717.

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9

Banerjee, Bubun. "Microwave-assisted Carbon-Carbon and Carbon-Heteroatom Bond Forming Reactions - Part 1B." Current Microwave Chemistry 7, no. 2 (2020): 84–85. http://dx.doi.org/10.2174/221333560702200714141435.

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10

Banerjee, Bubun. "Microwave-assisted Carbon-Carbon and Carbon-Heteroatom Bond Forming Reactions - Part 2A." Current Microwave Chemistry 8, no. 2 (2021): 56–57. http://dx.doi.org/10.2174/221333560802211028163413.

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11

Banerjee, Bubun. "Microwave-Assisted Carbon-Carbon and Carbon-Heteroatom Bond Forming Reactions: Part 2B." Current Microwave Chemistry 8, no. 3 (2021): 138–39. http://dx.doi.org/10.2174/221333560803211230153553.

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12

Leyva-Pérez, A. "Sub-nanometre metal clusters for catalytic carbon–carbon and carbon–heteroatom cross-coupling reactions." Dalton Transactions 46, no. 46 (2017): 15987–90. http://dx.doi.org/10.1039/c7dt03203j.

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13

Deng, Yu-Hua, Zhihui Shao, and Hui Wang. "An Update of N-Tosylhydrazones: Versatile Reagents for Metal-Catalyzed and Metal-Free Coupling Reactions." Synthesis 50, no. 12 (2018): 2281–306. http://dx.doi.org/10.1055/s-0036-1591993.

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N-Tosylhydrazones have had widespread application in organic synthesis for more than a half century. In most of cases, N-tosylhydrazones, as masked diazo compounds, have been generally used in a series of important carbon–carbon and carbon–heteroatom bond-forming reactions. This review provides an update on progress in diverse coupling reactions of N-tosylhydrazones since 2012. The examples selected are mainly categorized by metal-catalyzed and metal-free systems, wherein four main types of transformations including insertion, olefination, alkynylation, and cyclization are discussed for each s

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14

Banerjee, Bubun. "Carbon-carbon and Carbon-heteroatom Bond Forming Reactions Under Greener Conditions - Part 2." Current Organic Chemistry 25, no. 1 (2021): 2–3. http://dx.doi.org/10.2174/138527282501210101161748.

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15

Banerjee, Bubun. "Carbon-Carbon and Carbon-Heteroatom Bond-forming Reactions under Greener Conditions-Part 1A." Current Organic Chemistry 23, no. 28 (2020): 3135–36. http://dx.doi.org/10.2174/138527282328200117095904.

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16

Banerjee, Bubun. "Carbon-Carbon and Carbon-Heteroatom Bond-forming Reactions under Greener Conditions-Part 1B." Current Organic Chemistry 24, no. 1 (2020): 2–3. http://dx.doi.org/10.2174/138527282401200305142223.

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17

Banerjee, Bubun. "Carbon-carbon and Carbon-heteroatom Bond Forming Reactions Under Greener Conditions - Part 2." Current Organic Chemistry 25, no. 1 (2021): 2–3. http://dx.doi.org/10.2174/138527282501210101161748.

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18

Ajvazi, Njomza, and Stojan Stavber. "Alcohols in direct carbon-carbon and carbon-heteroatom bond-forming reactions: recent advances." Arkivoc 2018, no. 2 (2018): 288–329. http://dx.doi.org/10.24820/ark.5550190.p010.237.

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19

Brahmachari, Goutam, and Bubun Banerjee. "Sulfamic Acid-Catalyzed Carbon-Carbon and Carbon-Heteroatom Bond Forming Reactions: An Overview." Current Organocatalysis 3, no. 2 (2016): 93–124. http://dx.doi.org/10.2174/2213337202666150812230830.

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20

Kamanna, Kantharaju, and Santosh Y. Khatavi. "Microwave-accelerated Carbon-carbon and Carbon-heteroatom Bond Formation via Multi-component Reactions: A Brief Overview." Current Microwave Chemistry 7, no. 1 (2020): 23–39. http://dx.doi.org/10.2174/2213346107666200218124147.

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Multi-Component Reactions (MCRs) have emerged as an excellent tool in organic chemistry for the synthesis of various bioactive molecules. Among these, one-pot MCRs are included, in which organic reactants react with domino in a single-step process. This has become an alternative platform for the organic chemists, because of their simple operation, less purification methods, no side product and faster reaction time. One of the important applications of the MCRs can be drawn in carbon- carbon (C-C) and carbon-heteroatom (C-X; X = N, O, S) bond formation, which is extensively used by the organic

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21

Banerjee, Bubun. "Sc(OTf)3 catalyzed carbon-carbon and carbon-heteroatom bond forming reactions: a review." Arkivoc 2017, no. 1 (2016): 1–25. http://dx.doi.org/10.24820/ark.5550190.p009.868.

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22

Chen, Yi-Hung, Mario Ellwart, Vladimir Malakhov, and Paul Knochel. "Solid Organozinc Pivalates: A New Class of Zinc Organometallics with Greatly Enhanced Air- and Moisture-Stability." Synthesis 49, no. 15 (2017): 3215–23. http://dx.doi.org/10.1055/s-0036-1588843.

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Organozinc species are powerful reagents for performing carbon–carbon and carbon–heteroatom bond-forming reactions in the presence of a transition-metal catalyst. However, extended applications of zinc reagents have been hampered by their moderate air- and moisture-stability. This short review presents our recent developments on the preparation of solid aryl, benzyl, heteroaryl, allyl zinc pivalates and zinc amide enolate reagents with greatly enhanced stability toward to air and moisture.1 Introduction2 Preparation of Organozinc Pivalates2.1 Using Organic Halides as Substrates2.2 Using a Dir

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23

Nair, Vijay, Sreeletha B. Panicker, Latha G. Nair, Tesmol G. George, and Anu Augustine. "Carbon-Heteroatom Bond-Forming Reactions Mediated by Cerium(IV) Ammonium Nitrate:An Overview." Synlett, no. 2 (2003): 0156–65. http://dx.doi.org/10.1055/s-2003-36775.

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24

Teichert, Johannes F., and Lea T. Brechmann. "Catch It If You Can: Copper-Catalyzed (Transfer) Hydrogenation Reactions and Coupling Reactions by Intercepting Reactive Intermediates Thereof." Synthesis 52, no. 17 (2020): 2483–96. http://dx.doi.org/10.1055/s-0040-1707185.

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The key reactive intermediate of copper(I)-catalyzed alkyne semihydrogenations is a vinylcopper(I) complex. This intermediate can be exploited as a starting point for a variety of trapping reactions. In this manner, an alkyne semihydrogenation can be turned into a dihydrogen-mediated coupling reaction. Therefore, the development of copper-catalyzed (transfer) hydrogenation reactions is closely intertwined with the corresponding reductive trapping reactions. This short review highlights and conceptualizes the results in this area so far, with H2-mediated carbon–carbon and carbon–heteroatom bon

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25

Terao, Jun, Hirohisa Todo, Hiroyasu Watabe, Aki Ikumi, Yoshiaki Shinohara, and Nobuaki Kambe. "Carbon-carbon bond-forming reactions using alkyl fluorides." Pure and Applied Chemistry 80, no. 5 (2008): 941–51. http://dx.doi.org/10.1351/pac200880050941.

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This account reviews C-C bond formation reactions using alkyl fluorides mostly focusing on the transition-metal-catalyzed reactions. These reactions proceed efficiently under mild conditions by the combined use of Grignard reagents and transition-metal catalysts, such as Ni, Cu, and Zr. It is proposed that ate complex intermediates formed by the reaction of these transition metals with Grignard reagents play important roles as the active catalytic species. Organoaluminun reagents react directly with alkyl fluorides in nonpolar solvents at room temperature to form C-C bonds. These studies demon

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26

Ranu, Brindaban C., Tanmay Chatterjee, and Nirmalya Mukherjee. "ChemInform Abstract: Carbon-Heteroatom Bond Forming Reactions and Heterocycle Synthesis under Ball Milling." ChemInform 46, no. 25 (2015): no. http://dx.doi.org/10.1002/chin.201525284.

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27

Bhunia, Anup, Santhivardhana Reddy Yetra, and Akkattu T. Biju. "Recent advances in transition-metal-free carbon–carbon and carbon–heteroatom bond-forming reactions using arynes." Chemical Society Reviews 41, no. 8 (2012): 3140. http://dx.doi.org/10.1039/c2cs15310f.

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28

Brahmachari, Goutam, Nayana Nayek, Mullicka Mandal, Anindita Bhowmick, and Indrajit Karmakar. "Ultrasound-promoted Organic Synthesis - A Recent Update." Current Organic Chemistry 25, no. 13 (2021): 1539–65. http://dx.doi.org/10.2174/1385272825666210316122319.

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Abstract: Ultrasonication, nowadays, is well-regarded as an effective green tool in implementing a plethora of organic transformations. The last decade has seen quite useful applications of ultrasound irradiation in synthetic organic chemistry. Ultrasound has already come out as a unique technique in green chemistry practice for its inherent properties of minimizing wastes and reducing energy and time, thereby increasing the product yields with higher purities under milder reaction conditions. The present review summarizes ultrasound-promoted useful organic transformations involving both carbo

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29

Majumdar, K. C., B. Roy, P. Debnath, and A. Taher. "Metal-mediated Heterocyclization: Synthesis of Heterocyclic Compounds Containing More Than One Heteroatom Through Carbon-Heteroatom Bond Forming Reactions." Current Organic Chemistry 14, no. 8 (2010): 846–87. http://dx.doi.org/10.2174/138527210791111876.

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30

Yoda, Hidemi, Tetsuya Sengoku, Tomoya Hamamatsu, Toshiyasu Inuzuka, and Masaki Takahashi. "New Synthetic Methodology toward Macrolides/Macrolactams via Palladium-Catalyzed Carbon-Heteroatom Bond-Forming Reactions." Synlett 2011, no. 12 (2011): 1766–68. http://dx.doi.org/10.1055/s-0030-1260812.

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31

Zhu, Rong. "Emerging Catalyst Control in Cobalt-Catalyzed Oxidative Hydrofunctionalization Reactions." Synlett 30, no. 18 (2019): 2015–21. http://dx.doi.org/10.1055/s-0039-1690498.

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Oxidative functionalization has emerged as an important pathway in Co-catalyzed hydrogen atom transfer (HAT) hydrofunctionalization reactions. Notably, evidence was found for the participation of organometallic intermediates in such radical-polar crossover processes. These findings provide opportunities for catalyst control that was previously absent in HAT catalysis. In this article, we summarize the recent progress towards this direction involving carbon–heteroatom bond-forming intra- and intermolecular reactions, including work from our own group.1 Introduction2 Oxidative Trapping by Solven

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32

Oliver-Meseguer, Judit, Antonio Leyva-Pérez, and Avelino Corma. "Very Small (3-6 Atoms) Gold Cluster Catalyzed Carbon-Carbon and Carbon-Heteroatom Bond-Forming Reactions in Solution." ChemCatChem 5, no. 12 (2013): 3509–15. http://dx.doi.org/10.1002/cctc.201300695.

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33

Bhunia, Anup, Santhivardhana Reddy Yetra, and Akkattu T. Biju. "ChemInform Abstract: Recent Advances in Transition-Metal-Free Carbon-Carbon and Carbon-Heteroatom Bond-Forming Reactions Using Arynes." ChemInform 43, no. 30 (2012): no. http://dx.doi.org/10.1002/chin.201230238.

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34

Lorsbach, Beth A., and Mark J. Kurth. "Carbon−Carbon Bond Forming Solid-Phase Reactions." Chemical Reviews 99, no. 6 (1999): 1549–82. http://dx.doi.org/10.1021/cr970109y.

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35

Majumdar, K. C., B. Roy, P. Debnath, and A. Taher. "ChemInform Abstract: Metal-Mediated Heterocyclization: Synthesis of Heterocyclic Compounds Containing More than One Heteroatom Through Carbon-Heteroatom Bond-Forming Reactions." ChemInform 41, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.201035243.

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36

Correa, Arkaitz, та Marcos Segundo. "Cross-Dehydrogenative Coupling Reactions for the Functionalization of α-Amino Acid Derivatives and Peptides". Synthesis 50, № 15 (2018): 2853–66. http://dx.doi.org/10.1055/s-0037-1610073.

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The functionalization of typically unreactive C(sp3)–H bonds holds great promise for reducing the reliance on existing functional groups while improving atom-economy and energy efficiency. As a result, this topic is a matter of genuine concern for scientists in order to achieve greener chemical processes. The site-specific modification of α-amino acid and peptides based upon C(sp3)–H functionalization still represents a great challenge of utmost synthetic importance. This short review summarizes the most recent advances in ‘Cross-Dehydrogenative Couplings’ of α-amino carbonyl compounds and pep

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37

Chauhan, Pankaj, Suruchi Mahajan, and Dieter Enders. "Organocatalytic Carbon–Sulfur Bond-Forming Reactions." Chemical Reviews 114, no. 18 (2014): 8807–64. http://dx.doi.org/10.1021/cr500235v.

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38

Bedford, Robin B. "Palladacyclic catalysts in C–C and C–heteroatom bond-forming reactions." Chem. Commun., no. 15 (2003): 1787–96. http://dx.doi.org/10.1039/b211298c.

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39

Sengoku, Tetsuya, Tomoya Hamamatsu, Toshiyasu Inuzuka, Masaki Takahashi, and Hidemi Yoda. "ChemInform Abstract: New Synthetic Methodology Toward Macrolides/Macrolactams via Palladium-Catalyzed Carbon-Heteroatom Bond-Forming Reactions." ChemInform 42, no. 50 (2011): no. http://dx.doi.org/10.1002/chin.201150160.

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40

Oliver-Meseguer, Judit, Antonio Leyva-Perez, and Avelino Corma. "ChemInform Abstract: Very Small (3-6 Atoms) Gold Cluster Catalyzed Carbon-Carbon and Carbon-Heteroatom Bond-Forming Reactions in Solution." ChemInform 45, no. 16 (2014): no. http://dx.doi.org/10.1002/chin.201416027.

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41

NAKAMURA, Eiichi. "Carbon-carbon bond forming reactions via metal homoenolates." Journal of Synthetic Organic Chemistry, Japan 47, no. 10 (1989): 931–38. http://dx.doi.org/10.5059/yukigoseikyokaishi.47.931.

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42

SUZUKI, Hitomi, Hajime MANABE, and Masahiko INOUYE. "Sodium telluride-mediated carbon-carbon bond-forming reactions." NIPPON KAGAKU KAISHI, no. 7 (1987): 1485–89. http://dx.doi.org/10.1246/nikkashi.1987.1485.

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43

Cossy, Janine, François Lutz, Valérie Alauze, and Christophe Meyer. "Carbon-Carbon Bond Forming Reactions by using Bistrifluoromethanesulfonimide." Synlett 2002, no. 01 (2002): 0045–48. http://dx.doi.org/10.1055/s-2002-19329.

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44

Ravelli, Davide, Stefano Protti, and Maurizio Fagnoni. "Carbon–Carbon Bond Forming Reactions via Photogenerated Intermediates." Chemical Reviews 116, no. 17 (2016): 9850–913. http://dx.doi.org/10.1021/acs.chemrev.5b00662.

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45

Mayr, Herbert, Bernhard Kempf та Armin R. Ofial. "π-Nucleophilicity in Carbon−Carbon Bond-Forming Reactions". Accounts of Chemical Research 36, № 1 (2003): 66–77. http://dx.doi.org/10.1021/ar020094c.

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46

Ziegler, Frederick E., and Yizhe Wang. "Carbon-carbon bond forming reactions with oxiranyl radicals." Tetrahedron Letters 37, no. 35 (1996): 6299–302. http://dx.doi.org/10.1016/0040-4039(96)01384-6.

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47

Yurovskaya, M. A., and O. D. Mit'kin. "Functionalization of pyridines. 3. Reactions forming a carbon-heteroatom bond with group IV, V, and VI elements." Chemistry of Heterocyclic Compounds 35, no. 4 (1999): 383–435. http://dx.doi.org/10.1007/bf02319329.

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48

Rossi, Renzo, Fabio Bellina, and Adriano Carpita. "ChemInform Abstract: Development and Applications of Selective Palladium-Catalyzed Carbon-Carbon Bond and Carbon-Heteroatom Bond Forming Reactions Which Involve Stereodefined 2,3-Dibromo-2-alkenoates." ChemInform 30, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.199950272.

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49

Babu, Srinivasarao A., Ramasamy V. Anand, and Sripada S. V. Ramasastry. "Cinchona Alkaloid-Catalyzed Stereoselective Carbon-Carbon Bond Forming Reactions." Recent Patents on Catalysis 2, no. 1 (2013): 47–67. http://dx.doi.org/10.2174/2211548x11302010003.

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50

OKU, Akira, and Toshiro HARADA. "Selective carbon-carbon bond forming reactions utilizing carbene reaction." Journal of Synthetic Organic Chemistry, Japan 44, no. 8 (1986): 736–55. http://dx.doi.org/10.5059/yukigoseikyokaishi.44.736.

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