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
相关论文
共 50 条
  • [21] A TiO2 immobilized Ru(II) polyazine complex: a visible-light active photoredox catalyst for oxidative cyanation of tertiary amines
    Kumar, Pawan
    Varma, Sanny
    Jain, Suman L.
    JOURNAL OF MATERIALS CHEMISTRY A, 2014, 2 (13) : 4514 - 4519
  • [22] Controllable Chemoselectivity in Visible-Light Photoredox Catalysis: Four Diverse Aerobic Radical Cascade Reactions
    Liu, Xinfei
    Ye, Xinyi
    Bures, Filip
    Liu, Hongjun
    Jiang, Zhiyong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (39) : 11443 - 11447
  • [23] Photocatalytic Oxidation of Lignin Model Systems by Merging Visible-Light Photoredox and Palladium Catalysis
    Karkas, Markus D.
    Bosque, Irene
    Matsuura, Bryan S.
    Stephenson, Corey R. J.
    ORGANIC LETTERS, 2016, 18 (19) : 5166 - 5169
  • [24] Steered polymorphic nanodomains in TiO2 to boost visible-light photocatalytic oxidation
    Zhang, Zeju
    Niu, Mang
    Li, Wei
    Ding, Chenfeng
    Xie, Peitao
    Li, Yongxin
    Chen, Lili
    Lan, Xiaopeng
    Liu, Chunlei
    Yan, Xiaodong
    Fu, Xuewei
    Liu, Yaochun
    Liu, Yuan
    Cao, Dapeng
    Dai, Jingjie
    Hong, Xiaofen
    Liu, Chunzhao
    RSC ADVANCES, 2022, 12 (16) : 9660 - 9670
  • [25] (Zn,Fe)-Doped Palygorskite Loaded TiO2 for Visible-Light Active Catalysis
    Zhao, Difang
    Tian, Changan
    Lu, Hongdian
    ASIAN JOURNAL OF CHEMISTRY, 2012, 24 (09) : 4071 - 4072
  • [26] Metalloligand Hybrid Polyoxometalates for Efficient Selective Photocatalytic Oxidation of Sulfides to Sulfoxides under Visible-Light Irradiation
    Ji, Kaihui
    Liu, Yanan
    Luo, Yinghua
    Zhang, Xue
    Bai, Yufan
    Yue, Hailong
    Ma, Pengtao
    Niu, Jingyang
    Wang, Jingping
    JOURNAL OF PHYSICAL CHEMISTRY C, 2023, 127 (01): : 256 - 264
  • [27] Disordered mesoporous V/TiO2 system for ambient oxidation of sulfides to sulfoxides
    Negi, Sanjay Singh
    Sivaranjani, Kumarsrinivasan
    Singh, Anand Pal
    Gopinath, Chinnakonda S.
    APPLIED CATALYSIS A-GENERAL, 2013, 452 : 132 - 138
  • [28] VISIBLE-LIGHT RESPONSE OF POLYCRYSTALLINE TIO2 ELECTRODES
    MATSUMOTO, Y
    KURIMOTO, J
    AMAGASAKI, Y
    SATO, E
    JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 1980, 127 (10) : 2148 - 2152
  • [29] Visible-light promoted photocatalyst-free aerobic α-oxidation of tertiary amines to amides
    Xie, Xinpeng
    Guo, Xuan
    Qiao, Kaikai
    Shi, Lei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (41) : 8031 - 8036
  • [30] Utilization of CO2 Feedstock for Organic Synthesis by Visible-Light Photoredox Catalysis
    Pradhan, Suman
    Roy, Sourav
    Sahoo, Basudev
    Chatterjee, Indranil
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (07) : 2254 - 2269