Literature DB >> 28853571

Electrochemical Decarboxylative Sulfonylation of Cinnamic Acids with Aromatic Sulfonylhydrazides to Vinyl Sulfones.

Yu Zhao1, Yin-Long Lai1, Ke-Si Du1, Dian-Zhao Lin1, Jing-Mei Huang1.   

Abstract

A stereoselective synthesis of (E)-vinyl sulfones has been developed via electrochemical oxidative N-S bond cleavage of aromatic sulfonylhydrazides, followed by cross-coupling reactions with cinnamic acids to form the C-S bond. The protocol proceeded smoothly to afford (E)-vinyl sulfones in good yields with wide substrate scope under metal-free and halogen-free conditions.

Entities:  

Year:  2017        PMID： 28853571     DOI： 10.1021/acs.joc.7b01741

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  5 in total

Review 1.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

Review 2.  Recent Progress and Emerging Technologies towards a Sustainable Synthesis of Sulfones.

Authors:  Shuai Liang; Kamil Hofman; Marius Friedrich; Julian Keller; Georg Manolikakes
Journal:  ChemSusChem       Date:  2021-10-13       Impact factor: 9.140

Review 3.  Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis.

Authors:  Rik H Verschueren; Wim M De Borggraeve
Journal:  Molecules       Date:  2019-06-05       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.  Quick construction of a C-N bond from arylsulfonyl hydrazides and Csp2-X compounds promoted by DMAP at room temperature.

Authors:  Kai Yang; Juan-Juan Gao; Shi-He Luo; Han-Qing Wu; Chu-Ming Pang; Bo-Wen Wang; Xiao-Yun Chen; Zhao-Yang Wang
Journal:  RSC Adv       Date:  2019-06-26       Impact factor: 3.361
  5 in total

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