Issue 17, 2018

Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts

Abstract

A general, highly selective method for decarbonylative thioetherification of aryl thioesters by C–S cleavage is reported. These reactions are promoted by a commercially-available, user-friendly, inexpensive, air- and moisture-stable nickel precatalyst. The process occurs with broad functional group tolerance, including free anilines, cyanides, ketones, halides and aryl esters, to efficiently generate thioethers using ubiquitous carboxylic acids as ultimate cross-coupling precursors (cf. conventional aryl halides or pseudohalides). Selectivity studies and site-selective orthogonal cross-coupling/thioetherification are described. This thioester activation/coupling has been highlighted in the expedient synthesis of biorelevant drug analogue. In light of the synthetic utility of thioethers and Ni(II) precatalysts, we anticipate that this user-friendly method will be of broad interest.

Graphical abstract: Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts

Supplementary files

Article information

Article type
Communication
Submitted
12 Jan 2018
Accepted
30 Jan 2018
First published
30 Jan 2018

Chem. Commun., 2018,54, 2130-2133

Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts

C. Liu and M. Szostak, Chem. Commun., 2018, 54, 2130 DOI: 10.1039/C8CC00271A

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