Disulfide-Catalyzed Visible-Light-Mediated Oxidative Cleavage of C=C Bonds and Evidence of an Olefin-Disulfide Charge-Transfer Complex

被引：137
|
作者：
Deng, Yuchao [1 ,2 ,3 ]
Wei, Xiao-Jing [4 ]
Wang, Hui [1 ]
Sun, Yuhan [1 ,2 ]
Noel, Timothy [4 ]
Wang, Xiao [1 ,5 ,6 ]
机构：
[1] Chinese Acad Sci, Shanghai Adv Res Inst, CAS Key Lab Low Carbon Convers Sci & Engn, 100 Haike Rd, Shanghai 201210, Peoples R China
[2] ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China
[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[4] Eindhoven Univ Technol, Micro Flow Chem & Proc Technol, Dept Chem Engn & Chem, Den Dolech 2, NL-5612 AZ Eindhoven, Netherlands
[5] Harvard Med Sch, Harvard NeuroDiscovery Ctr, 65 Landsdowne St, Cambridge, MA 02139 USA
[6] Brigham & Womens Hosp, 65 Landsdowne St, Cambridge, MA 02139 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 03期
关键词：
disulfide catalysts; donor-acceptor complexes; olefin oxidation; organocatalysis; visible-light photocatalysis; COOXIDATION TOCO REACTION; SUBSTITUTED BENZENETHIYL RADICALS; GEM-DISUBSTITUTED ALKENES; C DOUBLE-BOND; MOLECULAR-OXYGEN; FLASH-PHOTOLYSIS; VINYL MONOMERS; ADDITION RATES; THIYL RADICALS; ELECTRON-TRANSFER;
D O I：
10.1002/anie.201607948
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A photocatalytic method for the aerobic oxidative cleavage of C=C bonds has been developed. Electron-rich aromatic disulfides were employed as photocatalyst. Upon visible-light irradiation, typical mono- and multi-substituted aromatic olefins could be converted into ketones and aldehydes at ambient temperature. Experimental and computational studies suggest that a disulfide-olefin charge-transfer complex is possibly responsible for the unconventional dissociation of S-S bond under visible light.
引用
收藏
页码：832 / 836
页数：5
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