Metal-free C-S coupling of thiols and disulfides

被引:49
|
作者
Pramanik, Milan [1 ]
Choudhuri, Khokan [1 ]
Mal, Prasenjit [1 ]
机构
[1] HBNI, Natl Inst Sci Educ & Res NISER, Sch Chem Sci, PO Bhimpur Padanpur,Via Jatni, Bhubaneswar 752050, Odisha, India
关键词
REGIOSELECTIVE SULFENYLATION; BOND FORMATION; EFFICIENT ACCESS; FACILE ACCESS; KETO ACIDS; THIOPHENOLS; THIOLATION; OXIDATION; IMIDAZOHETEROCYCLES; ALKENES;
D O I
10.1039/d0ob01741h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In organic synthesis, transition-metal and photoredox-catalysis-based reaction systems are emerging trends for the construction of C-S bonds. Many review articles have recently appeared in this field; however, we present herein an overview of metal-free C-S coupling reactions using thiols or disulfides as sulfur surrogates. The oxidants we have considered include peroxides, tert-butyl nitrite (TBN), DDQ, iodine reagents, and molecular oxygen. In addition, selective electrochemical oxidative transformations are also covered with mechanistic details.
引用
收藏
页码:8771 / 8792
页数:22
相关论文
共 50 条
  • [1] Photochemical metal-free aerobic oxidation of thiols to disulfides
    Spiliopoulou, Nikoleta
    Kokotos, Christoforos G.
    [J]. GREEN CHEMISTRY, 2021, 23 (01) : 546 - 551
  • [2] A metal-free desulfurizing radical reductive C-C coupling of thiols and alkenes
    Qin, Qixue
    Wang, Weijing
    Zhang, Cheng
    Song, Song
    Jiao, Ning
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (71) : 10583 - 10586
  • [3] Transition metal-free and regioselective alkenyl C-S cross-coupling reaction of alkenylsulfonium salts
    Wang, Qiang
    Wu, Shuaijie
    Wang, Yi-Dong
    Sun, Jing
    Han, Ying
    Yan, Chao-Guo
    Wang, Lei
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (12) : 2907 - 2912
  • [4] Metal-Free Oxidative Thioesterification of Methyl Ketones with Thiols/Disulfides for the Synthesis of α-Ketothioesters
    Hu, Biao
    Zhou, Pan
    Zhang, Qiaohe
    Wang, Yanqin
    Zhao, Siyun
    Lu, Lingling
    Yan, Shengjiao
    Yu, Fuchao
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (24): : 14978 - 14986
  • [5] Rapid synthesis of aryl sulfides through metal-free C-S coupling of thioalcohols with diaryliodonium salts
    Wang, Dawei
    Yu, Xin
    Zhao, Keyan
    Li, Liang
    Ding, Yuqiang
    [J]. TETRAHEDRON LETTERS, 2014, 55 (42) : 5739 - 5741
  • [6] Metal-free oxidative coupling of thiols to disulfides using guanidinium nitrate or nitro urea in the presence of silica sulfuric acid
    Ghorbani-Choghamarani, Arash
    Nikoorazm, Mohsen
    Goudarziafshar, Hamid
    Shokr, Alireza
    Almasi, Hosein
    [J]. JOURNAL OF CHEMICAL SCIENCES, 2011, 123 (04) : 453 - 457
  • [7] Metal-free oxidative coupling of thiols to disulfides using guanidinium nitrate or nitro urea in the presence of silica sulfuric acid
    ARASH GHORBANI-CHOGHAMARANI
    MOHSEN NIKOORAZM
    HAMID GOUDARZIAFSHAR
    ALIREZA SHOKR
    HOSEIN ALMASI
    [J]. Journal of Chemical Sciences, 2011, 123 : 453 - 457
  • [8] Metal-Free Photocatalytic Aerobic Oxidation of Thiols to Disulfides in Batch and Continuous-Flow
    Talla, Ali
    Driessen, Brian
    Straathof, Natan J. W.
    Milroy, Lech-Gustav
    Brunsveld, Luc
    Hessel, Volker
    Noel, Timothy
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (10) : 2180 - 2186
  • [9] Ligand-free copper-catalyzed C-S coupling of aryl iodides and thiols
    Sperotto, Elena
    van Klink, Gerard P. M.
    de Vries, Johannes G.
    van Koten, Gerard
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14): : 5625 - 5628
  • [10] Metal-Free Visible-light Mediated C-S Bond Formation
    Sahoo, Ashish Kumar
    Barik, Dinabandhu
    Dam, Binoyargha
    Patel, Bhisma K.
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (08)