Copper-Catalyzed Vicinal Chloro-thiolation of Alkynes with Sulfonyl Chlorides

被引：42
|
作者：
Liang, Shuaishuai [1 ]
Jiang, Lvqi [1 ]
Yi, Wen-bin [1 ]
Wei, Jingjing [1 ]
机构：
[1] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing 210094, Jiangsu, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 22期
基金：
中国国家自然科学基金;
关键词：
SULFENYL CHLORIDES; TERMINAL ALKYNES; VINYL SULFIDE; PALLADIUM; CHEMISTRY; FUNCTIONALIZATION; ANTIBIOTICS; ACETYLENES; COUPLINGS; BONDS;
D O I：
10.1021/acs.orglett.8b02929
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper-catalyzed vicinal chloro-thiolation of alkynes with inexpensive and diversified sulfonyl chlorides RSO2Cl (R = aryl, alkyl) has been developed. This practical and scalable reaction could be used for the construction of a number of unexplored bioactive chlorothiolated alkenes. Internal alkynes could also undergo the chloro-thiolation to provide tetrasubstituted alkynes. Preliminary mechanistic investigations revealed a plausible radical process involving a sulfur-centered radical intermediate via copper-mediated homolysis of the S-Cl bond.
引用
收藏
页码：7024 / 7028
页数：5
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