NBS-Promoted Sulfenylation of Sulfinates with Disulfides Leading to Unsymmetrical or Symmetrical Thiosulfonates

被引:55
作者
Liang Gaigai [1 ]
Liu Miaochang [1 ]
Chen Jiuxi [1 ]
Ding Jinchang [1 ,2 ]
Gao Wenxia [1 ]
Wu Huayue [1 ]
机构
[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Zhejiang, Peoples R China
[2] Wenzhou Vocat & Tech Coll, Wenzhou 325035, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
sulfenylation; N-bromosuccinimide (NBS); sulfinate; disulfide; thiosulfonate; ARYLBORONIC ACIDS; CHARCOAL N2O4/CHARCOAL; SELECTIVE OXIDATION; ORGANIC DISULFIDES; CATALYZED ADDITION; CARBONYL-COMPOUNDS; FACILE SYNTHESIS; ESTER SYNTHESIS; S-ESTERS; ALDEHYDES;
D O I
10.1002/cjoc.201200028
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly practical method to access unsymmetrical and symmetrical thiosulfonates in moderate to excellent yields has been developed through NBS-promoted sulfenylation of sulfinates with disulfides. The present process enables the use of two RS in RSSR and shows broad functional group tolerance, which represents an atom-economical and practical procedure for the synthesis of thiosulfonates. A plausible mechanism for the role of NBS as a promoter for the cleavage of disul?des generating N-(organothio)succinimide that then undergos facile sulenylation with sulfinates is proposed.
引用
收藏
页码:1611 / 1616
页数:6
相关论文
共 48 条
[41]   Acid-Catalyzed Regioselective Sulfetherification of Alkenols and Stereoselective Rearrangement of Tetrahydrofuran to Tetrahydropyran [J].
Wang, Haining ;
Huang, Deshun ;
Cheng, Donghao ;
Li, Lijun ;
Shi, Yian .
ORGANIC LETTERS, 2011, 13 (07) :1650-1653
[42]   ALKYL + ARYL THIOLSULFONATES [J].
WEIDNER, JP ;
BLOCK, SS .
JOURNAL OF MEDICINAL CHEMISTRY, 1964, 7 (05) :671-&
[43]  
Xia M., 1997, SYNTHETIC COMMUN, V27, P1309
[44]   Palladium-catalyzed hydroarylation of alkynes with arylboronic acids [J].
Xu, Xiaoling ;
Chen, Jiuxi ;
Gao, Wenxia ;
Wu, Huayue ;
Ding, Jinchang ;
Su, Weike .
TETRAHEDRON, 2010, 66 (13) :2433-2438
[45]   TCCA-promoted solvent-free chemoselective synthesis of thiosulfonates on grinding [J].
Xu, Yali ;
Peng, Yong ;
Sun, Junhui ;
Chen, Jiuxi ;
Ding, Jinchang ;
Wu, Huayue .
JOURNAL OF CHEMICAL RESEARCH, 2010, (06) :358-360
[46]  
Zefirov N.S., 1993, SULFUR REPORTS, V14, P223
[47]   Copper(II) Acetate-Catalyzed Addition of Arylboronic Acids to Aromatic Aldehydes [J].
Zheng, Hanmei ;
Zhang, Qiang ;
Chen, Jiuxi ;
Liu, Miaochang ;
Cheng, Shuanghua ;
Ding, Jinchang ;
Wu, Huayue ;
Su, Weike .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (02) :943-945
[48]   The Coupling of Arylboronic Acids with Nitroarenes Catalyzed by Rhodium [J].
Zheng, Xingwang ;
Ding, Jinchang ;
Chen, Jiuxi ;
Gao, Wenxiao ;
Liu, Miaochang ;
Wu, Huayue .
ORGANIC LETTERS, 2011, 13 (07) :1726-1729