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Jing-Mei Huang

Bio: Jing-Mei Huang is an academic researcher from South China University of Technology. The author has contributed to research in topics: Hydrogen bond & Radical. The author has an hindex of 1, co-authored 1 publications receiving 31 citations.

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TL;DR: An electro-oxidative C(sp3)–H bond functionalization of acetonitrile with thiols to afford tetrasubstituted olefins with high stereoselectivity is shown and can be easily scaled up.
Abstract: Incorporation of nitrile groups into fine chemicals is of particular interest through C(sp3)-H bonds activation of alkyl nitriles in the synthetic chemistry due to the highly efficient atom economy. However, the direct α-functionalization of alkyl nitriles is usually limited to its enolate chemistry. Here we report an electro-oxidative C(sp3)-H bond functionalization of acetonitrile with aromatic/aliphatic mercaptans for the synthesis of sulfur-containing β-enaminonitrile derivatives. These tetrasubstituted olefin products are stereoselectively synthesized and the stereoselectivity is enhanced in the presence of a phosphine oxide catalyst. With iodide as a redox catalyst, activation of C(sp3)-H bond to produce cyanomethyl radicals proceeds smoothly at a decreased anodic potential, and thus highly chemoselective formation of C-S bonds and enamines is achieved. Importantly, the process is carried out at ambient temperature and can be easily scaled up.

50 citations


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TL;DR: A review of the photochemical and electrochemical applications of multi-site proton-coupled electron transfer (MS-PCET) in organic synthesis can be found in this paper.
Abstract: We present here a review of the photochemical and electrochemical applications of multi-site proton-coupled electron transfer (MS-PCET) in organic synthesis. MS-PCETs are redox mechanisms in which both an electron and a proton are exchanged together, often in a concerted elementary step. As such, MS-PCET can function as a non-classical mechanism for homolytic bond activation, providing opportunities to generate synthetically useful free radical intermediates directly from a wide variety of common organic functional groups. We present an introduction to MS-PCET and a practitioner's guide to reaction design, with an emphasis on the unique energetic and selectivity features that are characteristic of this reaction class. We then present chapters on oxidative N-H, O-H, S-H, and C-H bond homolysis methods, for the generation of the corresponding neutral radical species. Then, chapters for reductive PCET activations involving carbonyl, imine, other X═Y π-systems, and heteroarenes, where neutral ketyl, α-amino, and heteroarene-derived radicals can be generated. Finally, we present chapters on the applications of MS-PCET in asymmetric catalysis and in materials and device applications. Within each chapter, we subdivide by the functional group undergoing homolysis, and thereafter by the type of transformation being promoted. Methods published prior to the end of December 2020 are presented.

136 citations

Journal ArticleDOI
TL;DR: This work describes how halogenide anions are anodically oxidized into active species, which can be elemental halogen, halogen cations, or halogen radicals, and how these species react with substrates to generate halogenated products.
Abstract: In general, halogenide anions are anodically oxidized into active species, which can be elemental halogen, halogen cations, or halogen radicals. These species subsequently react with substrates, such as olefins, ketones, or amines, to generate halogenated products. We review the mechanisms of these reactions.

78 citations

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TL;DR: In this paper, a direct electrochemical oxidative cyclization of alkynoates and alkynamides with diselenides or disulfides for the synthesis of coumarins and quinolinones bearing a chalcogen functional group has been developed.

74 citations

Journal ArticleDOI
TL;DR: An electrochemical protocol to synthesize vinyl thiocyanates from decarboxylative coupling of cinnamic acids with NH4SCN in aqueous solution is reported, which provides thiOCyanation products with broad functional group tolerance under ambient conditions.

59 citations

Journal ArticleDOI
TL;DR: An environmentally friendly characteristic of this reaction is that it uses electricity as a valuable energy source for electrochemical synthesis of β-ketosulfones, which is more convenient and practical compared to previous approaches.

55 citations