Literature DB >> 24860978

Copper-catalyzed aerobic oxidative N-S bond functionalization for C-S bond formation: regio- and stereoselective synthesis of sulfones and thioethers.

Xianwei Li1, Yanli Xu, Wanqing Wu, Chang Jiang, Chaorong Qi, Huanfeng Jiang.   

Abstract

A regio- and stereoselective synthesis of sulfones and thioethers by means of Cu(I)-catalyzed aerobic oxidative N-S bond cleavage of sulfonyl hydrazides, followed by cross-coupling reactions with alkenes and aromatic compounds to form the C sp 2-S bond, is described herein. N2 and H2O are the byproducts of this transformation, thus offering an environmentally benign process with a wide range of potential applications in organic synthesis and medicinal chemistry.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH functionalization; copper; oxygen; sulfones; thioethers

Year:  2014        PMID: 24860978     DOI: 10.1002/chem.201402815

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  5 in total

1.  A new cascade halosulfonylation of 1,7-enynes toward 3,4-dihydroquinolin-2(1H)-ones via sulfonyl radical-triggered addition/6-exo-dig cyclization.

Authors:  Yi-Long Zhu; Bo Jiang; Wen-Juan Hao; Ai-Fang Wang; Jiang-Kai Qiu; Ping Wei; De-Cai Wang; Guigen Li; Shu-Jiang Tu
Journal:  Chem Commun (Camb)       Date:  2016-01-31       Impact factor: 6.222

2.  The fast and efficient KI/H2O2 mediated 2-sulfonylation of indoles and N-methylpyrrole in water.

Authors:  Jun Zhang; Zhong Wang; Lingjuan Chen; Yan Liu; Ping Liu; Bin Dai
Journal:  RSC Adv       Date:  2018-12-12       Impact factor: 4.036

3.  Visible-Light-Induced, Graphene Oxide-Promoted C3-Chalcogenylation of Indoles Strategy under Transition-Metal-Free Conditions.

Authors:  Qing Huang; Xiangjun Peng; Hong Li; Haiping He; Liangxian Liu
Journal:  Molecules       Date:  2022-01-25       Impact factor: 4.411

4.  Electrochemical sulfonylation of alkenes with sulfonyl hydrazides: a metal- and oxidant-free protocol for the synthesis of (E)-vinyl sulfones in water.

Authors:  Yin-Long Lai; Yunyan Mo; Shaoxi Yan; Shengling Zhang; Lejie Zhu; Jianmin Luo; Huishi Guo; Jianpeng Cai; Jianhua Liao
Journal:  RSC Adv       Date:  2020-09-08       Impact factor: 4.036

5.  Catalytic arylsulfonyl radical-triggered 1,5-enyne-bicyclizations and hydrosulfonylation of α,β-conjugates.

Authors:  Zhen-Zhen Chen; Shuai Liu; Wen-Juan Hao; Ge Xu; Shuo Wu; Jiao-Na Miao; Bo Jiang; Shu-Liang Wang; Shu-Jiang Tu; Guigen Li
Journal:  Chem Sci       Date:  2015-11-13       Impact factor: 9.825

  5 in total

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