Transition-Metal-Free Synthesis of Unsymmetrical Disulfides via Three-Component Reaction of Thiosulfonates, Thiourea and Alkyl halides

被引:11
作者
Wang, Dungai [1 ]
He, Quan [1 ]
Shi, Keqiang [1 ]
Xiong, Mingteng [1 ]
Zhou, Yifeng [2 ]
Pan, Yuanjiang [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
[2] China Jiliang Univ, Coll Life Sci, Hangzhou 310018, Peoples R China
基金
中国国家自然科学基金;
关键词
transition-metal-free; unsymmetrical disulfides; one-pot reaction; K2CO3-promoted;
D O I
10.1002/adsc.202100165
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A transition-metal-free approach to synthesize unsymmetrical disulfides is reported that relies on a K2CO3-promoted one-pot reaction of thiosulfonates, thiourea and alkyl halides under mild conditions. The protocol tolerates a wide range of substrates, leading to various types of unsymmetrical disulfides in moderate to excellent yields. More importantly, the late-stage modification of natural products and drug molecules was also achieved.
引用
收藏
页码:2767 / 2772
页数:6
相关论文
共 62 条
[31]   Perfluoroalkylation of Thiosulfonates: Synthesis of Perfluoroalkyl Sulfides [J].
Luo, Ziwei ;
Yang, Xinkan ;
Tsui, Gavin Chit .
ORGANIC LETTERS, 2020, 22 (15) :6155-6159
[32]   Recent advances in S-S bond formation [J].
Mandal, Bablee ;
Basu, Basudeb .
RSC ADVANCES, 2014, 4 (27) :13854-13881
[33]   Multifunctional novel Diallyl disulfide (DADS) derivatives with β-amyloid-reducing, cholinergic, antioxidant and metal chelating properties for the treatment of Alzheimer's disease [J].
Manral, Apra ;
Saini, Vikas ;
Meena, Poonam ;
Tiwari, Manisha .
BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (19) :6389-6403
[34]  
Miele M., 2020, ADV CATAL, V362, P1
[35]   One-pot thioetherification of aryl halides with thiourea and benzyl bromide in water catalyzed by Cu-grafted furfural imine-functionalized mesoporous SBA-15 [J].
Mondal, John ;
Modak, Arindam ;
Dutta, Arghya ;
Basu, Sohini ;
Jha, Shambhu Nath ;
Bhattacharyya, Dibyendu ;
Bhaumik, Asim .
CHEMICAL COMMUNICATIONS, 2012, 48 (64) :8000-8002
[36]   Recent Developments in the Synthesis of Unsymmetrical Disulfanes (Disulfides). A Review [J].
Musiejuk, Mateusz ;
Witt, Dariusz .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2015, 47 (02) :95-131
[37]   Synthesis and Biological Evaluation of Epidithio-, Epitetrathio-, and bis-(Methylthio)diketopiperazines: Synthetic Methodology, Enantioselective Total Synthesis of Epicoccin G, 8,8′-epi-ent-Rostratin B, Gliotoxin, Gliotoxin G, Emethallicin E, and Haematocin and Discovery of New Antiviral and Antimalarial Agents [J].
Nicolaou, K. C. ;
Lu, Min ;
Totokotsopoulos, Sotirios ;
Heretsch, Philipp ;
Giguere, Denis ;
Sun, Ya-Ping ;
Sarlah, David ;
Nguyen, Thu H. ;
Wolf, Ian C. ;
Smee, Donald F. ;
Day, Craig W. ;
Bopp, Selina ;
Winzeler, Elizabeth A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (41) :17320-17332
[38]   Phototropin-Inspired Chemoselective Synthesis of Unsymmetrical Disulfides: Aerobic Oxidative Heterocoupling of Thiols Using Flavin Photocatalysis [J].
Oka, Marina ;
Katsube, Daichi ;
Tsuji, Takeshi ;
Iida, Hiroki .
ORGANIC LETTERS, 2020, 22 (23) :9244-9248
[39]   Unsymmetrical Disulfides Synthesis via Sulfenium Ion [J].
Parida, Amarchand ;
Choudhuri, Khokan ;
Mal, Prasenjit .
CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (15) :2579-2583
[40]   9-Fluorenylmethyl (Fm) Disulfides: Biomimetic Precursors for Persulfides [J].
Park, Chung-Min ;
Johnson, Brett A. ;
Duan, Jicheng ;
Park, Jeong-Jin ;
Day, Jacob J. ;
Gang, David ;
Qian, Wei-Jun ;
Xian, Ming .
ORGANIC LETTERS, 2016, 18 (05) :904-907