Transition-metal mediated carbon-sulfur bond activation and transformations: an update

Carbon-sulfur bond cross-coupling has become more and more attractive as an alternative protocol to establish carbon-carbon and carbon-heteroatom bonds. Diverse transformations through transition-metal-catalyzed C-S bond activation and cleavage have recently been developed. This review summarizes th...

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Published inChemical Society reviews Vol. 49; no. 13; pp. 437 - 4359
Main Authors Lou, Jiang, Wang, Quannan, Wu, Ping, Wang, Hongmei, Zhou, Yong-Gui, Yu, Zhengkun
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 07.07.2020
Subjects
Activation
Aromatic compounds
Carbon
Carbon disulfide
Cleavage
Cross coupling
Ductile-brittle transition
Hydrazides
Organosulfur compounds
Reagents
Sulfonates
Sulfones
Sulfonium salts
Sulfur
Thiocyanates
Thioesters
Transition metals
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Summary:Carbon-sulfur bond cross-coupling has become more and more attractive as an alternative protocol to establish carbon-carbon and carbon-heteroatom bonds. Diverse transformations through transition-metal-catalyzed C-S bond activation and cleavage have recently been developed. This review summarizes the advances in transition-metal-catalyzed cross-coupling via carbon-sulfur bond activation and cleavage since late 2012 as an update of the critical review on the same topic published in early 2013 ( Chem. Soc. Rev. , 2013, 42 , 599-621), which is presented by the categories of organosulfur compounds, that is, thioesters, thioethers including heteroaryl, aryl, vinyl, alkyl, and alkynyl sulfides, ketene dithioacetals, sulfoxides including DMSO, sulfones, sulfonyl chlorides, sulfinates, thiocyanates, sulfonium salts, sulfonyl hydrazides, sulfonates, thiophene-based compounds, and C&z.dbd;S functionality-bearing compounds such as thioureas, thioamides, and carbon disulfide, as well as the mechanistic insights. An overview of C-S bond cleavage reactions with stoichiometric transition-metal reagents is briefly given. Theoretical studies on the reactivity of carbon-sulfur bonds by DFT calculations are also discussed. This review summarizes the advances in transition-metal-catalyzed cross-coupling via carbon-sulfur bond activation and cleavage since late 2012 as an update of the critical review published in early 2013 ( Chem. Soc. Rev. , 2013, 42 , 599-621).
Bibliography:Hongmei Wang obtained her PhD degree from the Research Institute of Chemical Defense (RICD), Beijing, China, in 2005. In December 2005, she joined Prof. Zhengkun Yu's group at DICP of CAS as a visiting scholar. She returned to RICD at Beijing in 2006. Now she works at the State Key Laboratory of NBC Protection for Civilian, RICD. Her research interests are focused on synthetic methodologies and organometallic catalysis.
Ping Wu studied chemistry at Liaoning University, Shenyang, China, and received her MSc degree in July 2006. Then she joined Prof. Zhengkun Yu's group at DICP of CAS as a research associate. She is currently studying towards a PhD degree under the supervision of Prof. Zhengkun Yu. Her current research interest is centered on transition-metal-catalyzed synthetic methodologies of N-heterocycles.
Zhengkun Yu obtained his PhD degree from Dalian Institute of Chemical Physics (DICP), CAS, in July of 1995. During October 1995-January 2003 he worked as a post-doctoral fellow or research associate in the laboratories of Prof. Rudolf Aumann (University of Münster, Germany), Prof. John G. Verkade (Iowa State University, USA), and Prof. Chuck Winter (Wayne State University, USA), and in Waseda University/Japan Corporation of Science and Technology (Tokyo, Japan). He returned to DICP as a "Hundred Talents Program of CAS" professor in February 2003. His research interests are organometallic catalysis and synthesis.
Yong-Gui Zhou obtained his PhD degree from Shanghai Institute of Organic Chemistry of CAS in 1999. Then he joined Xumu Zhang's group at the Pennsylvania State University as a post-doctoral fellow to work on asymmetric hydrogenation of N-heterocyclic compounds. In 2002, he began his independent academic career at DICP of CAS, where he is a professor of organic chemistry. His research interests include the development of catalytic asymmetric reactions, mechanistic elucidation, and asymmetric synthesis.
Jiang Lou studied chemical engineering and technology at Jiangnan University, Wuxi, China, and received his BSc degree in July 2014. In September 2014, he joined Prof. Zhengkun Yu's group at Dalian Institute of Chemical Physics (DICP), Chinese Academy of Sciences (CAS), to pursue a PhD degree. His current research interest is centered on transition-metal-catalyzed C-H bond functionalization.
Quannan Wang studied chemical engineering and technology at Hefei University of Technology, Hefei, China, and received his BSc degree in July 2014. In September 2014, he joined Prof. Zhengkun Yu's group at DICP of CAS to pursue a PhD degree, and received his PhD degree in July 2019. His current research interest is process development in fine chemicals industry.
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ISSN:0306-0012
1460-4744
DOI:10.1039/c9cs00837c