Literature DB >> 22728918

Copper-catalyzed aerobic oxidation and cleavage/formation of C-S bond: a novel synthesis of aryl methyl sulfones from aryl halides and DMSO.

Gaoqing Yuan1, Junhua Zheng, Xiaofang Gao, Xianwei Li, Liangbin Huang, Huoji Chen, Huanfeng Jiang.   

Abstract

With atmospheric oxygen as the oxidant, a novel copper(I)-catalyzed synthesis of aryl methyl sulfones from aryl halides and widely available DMSO is described. The procedure tolerates aryl halides with various functional groups (such as methoxy, acetyl, chloro, fluoro and nitro groups), which could afford aryl methyl sulfones in moderate to high yields. The copper-catalyzed aerobic oxidation and the cleavage/formation of C-S bond are the key steps for this transformation.

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Year:  2012        PMID: 22728918     DOI: 10.1039/c2cc32964f

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  6 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

Review 2.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

3.  Biomimetic Aerobic C-H Olefination of Cyclic Enaminones at Room Temperature: Development toward the Synthesis of 1,3,5-Trisubstituted Benzenes.

Authors:  Yi-Yun Yu; Gunda I Georg
Journal:  Adv Synth Catal       Date:  2014-04-14       Impact factor: 5.837

4.  CO/O2 assisted oxidative carbon-carbon and carbon-heteroatom bond cleavage for the synthesis of oxosulfonates from DMSO and olefins.

Authors:  Ailong Shao; Meng Gao; Songtao Chen; Tao Wang; Aiwen Lei
Journal:  Chem Sci       Date:  2016-12-07       Impact factor: 9.825

5.  One-Pot NBS-Promoted Synthesis of Imidazoles and Thiazoles from Ethylarenes in Water.

Authors:  Liang Chen; Huajian Zhu; Jiang Wang; Hong Liu
Journal:  Molecules       Date:  2019-03-04       Impact factor: 4.411

6.  An efficient approach for the synthesis of novel methyl sulfones in acetic acid medium and evaluation of antimicrobial activity.

Authors:  Gollapudi Ravi Kumar; Chandra Rao Dasireddy; Ravi Varala; Vijay Kotra; Hari Babu Bollikolla
Journal:  Turk J Chem       Date:  2020-10-26       Impact factor: 1.239

  6 in total

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