Tertiary amine mediated aerobic oxidation of sulfides into sulfoxides by visible-light photoredox catalysis on TiO2

被引:95
作者
Lang, Xianjun [1 ]
Hao, Wei [1 ]
Leow, Wan Ru [1 ]
Li, Shuzhou [1 ]
Zhao, Jincai [2 ]
Chen, Xiaodong [1 ]
机构
[1] Nanyang Technol Univ, Sch Mat Sci & Engn, Singapore 639798, Singapore
[2] Chinese Acad Sci, Key Lab Photochem, Beijing Natl Lab Mol Sci, Inst Chem, Beijing 100190, Peoples R China
基金
新加坡国家研究基金会;
关键词
LIQUID-PHASE OXIDATION; SELECTIVE OXIDATION; TITANIUM-DIOXIDE; PHOTOCATALYTIC OXIDATION; AROMATIC ALCOHOLS; SURFACE-REACTIONS; ELECTRON-TRANSFER; EFFICIENT; REDUCTION; IMINES;
D O I
10.1039/c5sc01813g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The selective oxidation of sulfides into sulfoxides receives much attention due to industrial and biological applications. However, the realization of this reaction with molecular oxygen at room temperature, which is of importance towards green and sustainable chemistry, remains challenging. Herein, we develop a strategy to achieve the aerobic oxidation of sulfides into sulfoxides by exploring the synergy between a tertiary amine and titanium dioxide via visible-light photoredox catalysis. Specifically, titanium dioxide can interact with triethylamine (TEA) to form a visible-light harvesting surface complex, preluding the ensuing selective redox reaction. Moreover, TEA, whose stability was demonstrated by a turnover number of 32, plays a critical role as a redox mediator by shuttling electrons during the oxidation of sulfide. This work suggests that the addition of a redox mediator is highly functional in establishing visible-light-induced reactions via heterogeneous photoredox catalysis.
引用
收藏
页码:5000 / 5005
页数:6
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