Aqueous Reaction of Alcohols, Organohalides, and Odorless Sodium Thiosulfate under Transition-Metal-Free Conditions: Synthesis of Unsymmetrical Aryl Sulfides via Dual C-S Bond Formation

被引:20
作者
Liu, Bei-Bei [1 ,2 ]
Chu, Xue-Qiang [1 ,2 ]
Liu, Huan [1 ,2 ]
Yin, Ling [3 ]
Wang, Shun-Yi [1 ,2 ]
Ji, Shun-Jun [1 ,2 ]
机构
[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China
[2] Soochow Univ, Collaborat Innovat Ctr Suzhou Nano Sci & Technol, Suzhou 215123, Peoples R China
[3] Jining Univ, Dept Chem & Chem Engn, Qufu 273155, Peoples R China
基金
中国国家自然科学基金;
关键词
ELEMENTAL SULFUR; BUNTE SALTS; COUPLING REACTIONS; SULFONES; 3-SULFENYLATION; ACTIVATION; REDUCTION; CHLORIDES; INDOLES; OXIDANT;
D O I
10.1021/acs.joc.7b01653
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A transition-metal-free process for the synthesis of unsymmetrical aryl sulfides via dual C-S bond formation by a one-pot three-component reaction of alcohols, organohalides, and odorless sodium thiosulfate in water has been developed. In addition, the aryl sulfides could also be prepared by the reaction of the corresponding alcohols and Bunte salts under the identical conditions. This protocol provides a green and efficient manner for the construction of various unsymmetrical aryl sulfides.
引用
收藏
页码:10174 / 10180
页数:7
相关论文
共 59 条
[1]   Direct episulfidation of alkenes and allenes with elemental sulfur and thiiranes as sulfur sources, catalyzed by molybdenum oxo complexes [J].
Adam, W ;
Bargon, RM ;
Schenk, WA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (13) :3871-3876
[2]   A Solvent- and Metal-Free Synthesis of 3-Chacogenyl-indoles Employing DMSO/I2 as an Eco-friendly Catalytic Oxidation System [J].
Azeredo, Juliano B. ;
Godoi, Marcelo ;
Martins, Guilherme M. ;
Silveira, Claudio C. ;
Braga, Antonio L. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09) :4125-4130
[3]   Unusual influence of the structures of transition metal complexes on catalytic C-S and C-Se bond formation under homogeneous and heterogeneous conditions [J].
Beletskaya, Irina P. ;
Ananikov, Valentine P. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (21) :3431-3444
[4]   Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].
Beletskaya, Irina P. ;
Ananikov, Valentine P. .
CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636
[5]   THE ORGANOSULFUR CHEMISTRY OF THE GENUS ALLIUM - IMPLICATIONS FOR THE ORGANIC-CHEMISTRY OF SULFUR [J].
BLOCK, E .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1992, 31 (09) :1135-1178
[6]   CONVENIENT SYNTHESIS OF UNSYMMETRICAL ARYL SULFIDES [J].
BOTTINO, F ;
FRADULLO, R ;
PAPPALARDO, S .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (13) :2793-2795
[7]   TBAI-Catalyzed/Water-Assisted Double C-S Bond Formations: An Efficient Approach to Sulfides through Metal-Free Three-Component Reactions [J].
Chu, Xue-Qiang ;
Xu, Xiao-Ping ;
Ji, Shun-Jun .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (40) :14181-14185
[8]   One-Pot Synthesis of Allylic Sulfones, Ketosulfones, and Triflyl Allylic Alcohols from Domino Reactions of Allylic Alcohols with Sulfinic Acid under Metal-Free Conditions [J].
Chu, Xue-Qiang ;
Meng, Hua ;
Xu, Xiao-Ping ;
Ji, Shun-Jun .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (32) :11359-11368
[9]   Metal-Catalyzed and Metal-Free Alkyne Hydrothiolation: Synthetic Aspects and Application Trends [J].
Dondoni, Alessandro ;
Marra, Alberto .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (19) :3955-3969
[10]   Zinc-Mediated Palladium-Catalyzed Formation of Carbon-Sulfur Bonds [J].
Eichman, Chad C. ;
Stambuli, James P. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) :4005-4008