Modified Chemoselective Reduction and Consecutive Regioselective Deuteration Reaction Catalyzed by B(C6F5)3

J Org Chem. 2023 Feb 17;88(4):1996-2005. doi: 10.1021/acs.joc.2c02137. Epub 2023 Jan 30.

Abstract

An efficient chemoselective reduction of isatin derivatives using catalyst B(C6F5)3, benzyldimethylsilane, and H2O is described. Notably, a small amount of water is shown to be a highly effective reaction promoter that decreases the reaction time and temperature for the synthesis of indolin-3-ones. Moreover, using method, excellent deuterium incorporation is achieved via the catalytic α-deuteration of indolin-3-ones using B(C6F5)3 and D2O.