Synthesis and reactivity of 2-(ethylthio)phenylcopper: A stable organocopper compound carrying an intramolecular sulfane ligand

Article abstract of DOI:10.1016/S0022-328X(96)06496-0

An unusually stable organocopper compound carrying an intramolecular sulfane ligand, 2-(ethylthio)phenylcopper, was synthesized via the reaction of the corresponding organolithium with a copper(I) halide (CuX). This compound was obtained in two forms: one is a salt-free compound which is insoluble in ordinary solvents, the other is a soluble complex of [2-(ethylthio)phenylcopper]₂·CuX composition. These compounds were either hydrolyzed or underwent a coupling reaction to produce a biphenyl when heated. While these organocoppers are less reactive towards various electrophiles than other known arylcoppers, the soluble complex gives ketones with acyl halides in low yields. The properties as well as the reactivities of the stable organocopper compounds are reported.