Visible-Light Photocatalytic Reduction of Sulfonium Salts as a Source of Aryl Radicals

被引:108
|
作者
Donck, Simon [1 ]
Baroudi, Abdulkader [1 ]
Fensterbank, Louis [1 ]
Goddard, Jean-Philippe [1 ]
Ollivier, Cyril [1 ]
机构
[1] Univ Paris 06, CNRS, UMR 7201, Inst Parisien Chim Mol, F-75005 Paris, France
关键词
carbon-carbon bond formation; photocatalysis; radical reactions; reduction; sulfonium salts; C-H ARYLATION; ELECTRON-TRANSFER; PHOTOREDOX CATALYSIS; BOND-CLEAVAGE; ELECTROCHEMICAL REDUCTION; ARYLBORONIC ACIDS; GRIGNARD-REAGENTS; SELENONIUM SALTS; REDOX CATALYSIS; DIAZONIUM SALTS;
D O I
10.1002/adsc.201300040
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Triarylsulfonium salts are prompted to undergo efficient homolytic reduction by single electron transfer under mild photocatalytic conditions. The liberated aryl radical can then participate in carbon-carbon bond formation processes with allyl sulfones and activated olefins. Triarylsulfonium salts emerge as a valuable and alternative source of aryl radicals for synthesis.
引用
收藏
页码:1477 / 1482
页数:6
相关论文
共 50 条
  • [1] Visible-Light Photocatalytic Reduction of Aryl Halides as a Source of Aryl Radicals
    Lan, Jihong
    Chen, Rongxiang
    Duo, Fangfang
    Hu, Menghui
    Lu, Xiaoyan
    MOLECULES, 2022, 27 (17):
  • [2] Visible-light Photocatalytic Alkylsulfonylation of Aroylhydrazides with Alkylsulfonyl Radicals
    Yang Min
    Ye Baibai
    Chen Jianqiang
    Wu Jie
    ACTA CHIMICA SINICA, 2022, 80 (01) : 11 - 15
  • [3] PHOTOCATALYTIC NITROGEN REDUCTION USING VISIBLE-LIGHT
    TENNAKONE, K
    WICKRAMANAYAKE, S
    FERNANDO, CAN
    ILEPERUMA, OA
    PUNCHIHEWA, S
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (14) : 1078 - 1080
  • [4] A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides
    Czyz, M. L.
    Weragoda, G. K.
    Monaghan, R.
    Connell, T. U.
    Brzozowski, M.
    Scully, A. D.
    Burton, J.
    Lupton, D. W.
    Polyzos, A.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (09) : 1543 - 1551
  • [5] Towards Visible-Light Photocatalytic Reduction of Hypercoordinated Silicon Species
    Levernier, Etienne
    Leveque, Christophe
    Derat, Etienne
    Fensterbank, Louis
    Ollivier, Cyril
    HELVETICA CHIMICA ACTA, 2020, 103 (01)
  • [6] XANTHATES AS A SOURCE OF STABILIZED CARBON CENTERED RADICALS USING VISIBLE-LIGHT
    MESTRE, F
    TAILHAN, C
    ZARD, SZ
    HETEROCYCLES, 1989, 28 (01) : 171 - 174
  • [7] Photocatalytic nanodiodes for visible-light photocatalysis
    Kim, HG
    Borse, PH
    Choi, WY
    Lee, JS
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (29) : 4585 - 4589
  • [8] PHOTOELECTROCATALYTIC REDUCTION OF 4-CHLOROBIPHENYL USING ANION RADICALS AND VISIBLE-LIGHT
    SHUKLA, SS
    RUSLING, JF
    JOURNAL OF PHYSICAL CHEMISTRY, 1985, 89 (15): : 3353 - 3358
  • [9] Visible-light photocatalytic trifluoromethylthiolation of aryldiazonium salts: conversion of amino group into trifluoromethylthiol group
    Zhao, Xia
    Zheng, Xiancai
    Tian, Miaomiao
    Tong, Yifan
    Yang, Bo
    Wei, Xianfu
    Qiu, Di
    Lu, Kui
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (18): : 2636 - 2640
  • [10] Aryl Azocyclopropeniums: Minimalist, Visible-Light Photoswitches
    Fink, Moritz
    Stauble, Jannik
    Weisgerber, Maite
    Carreira, Erick M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (14) : 9519 - 9525