Copper-Catalyzed Thiolation Cyclization of 1-Chloro-1,5-enynes with Sodium Hydrosulfide: Synthesis of CF₃-Containing 1H-Isothiochromenes

Abstract

A copper-catalyzed regio- and stereoselective 6-exo-dig cyclization of 1-chloro-1,5-enynes with sodium hydrosulfide has been developed. In the presence of copper(I) iodide and sodium tert-butoxide, a variety of (Z)-1-methylene-3-(trifluoromethyl)-1H-isothiochromenes were prepared in moderate to good yields via thiolation cyclization of 1-alkynyl-2-(2-chloro-3,3,3-trifluoroprop-1-enyl)benzenes with sodium hydrosulfide.

Key words

copper - thiolation - 6-exo-dig cyclization - 1H-isothiochromenes - sodium hydrosulfide

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• This compound was prepared from the Sonogashira reaction of 2-bromobenzaldehyde and phenylacetylene, and then reacted with CF₃CCl₃, see:

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