Copper-Catalyzed Vicinal Chloro-thiolation of Alkynes with Sulfonyl Chlorides
Shuaishuai Liang1, Lvqi Jiang1, Wen-Bin Yi1
1School of Chemical Engineering , Nanjing University of Science and Technology , Nanjing 210094 , P. R. China.
Abstract:
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.
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