Synthesis of Alkynyl Sulfides by Copper-Catalyzed Thiolation of Terminal Alkynes Using Thiosulfonates.

Authors:
Suguru Yoshida
Suguru Yoshida
Kyoto University
Japan
Takamitsu Hosoya
Takamitsu Hosoya
Tokyo Medical and Dental University
Japan

Org Lett 2019 05 19;21(9):3172-3177. Epub 2019 Apr 19.

Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering , Tokyo Medical and Dental University (TMDU) , 2-3-10 Kanda-Surugadai , Chiyoda-ku, Tokyo 101-0062 , Japan.

A mild and odorless copper-catalyzed thiolation of terminal alkynes with thiosulfonates is described. The broad substrate scope provides convenient access to a wide variety of sulfur-containing heterocycles. In particular, divergent benzoheteroles are efficiently prepared in a simple manner by thiolation of ethynylbenzenes bearing ortho-nucleophilic functional groups followed by iodocyclization.

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Source
http://pubs.acs.org/doi/10.1021/acs.orglett.9b00875
Publisher Site
http://dx.doi.org/10.1021/acs.orglett.9b00875DOI Listing
May 2019
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