Site-selective deuteration at the α-position of enals by an amine and bis(phenylsulfonyl)methane co-catalyzed H/D exchange reaction

Abstract

An amine and bis(phenylsulfonyl)methane co-catalyzed hydrogen–deuterium exchange (HDE) method via a Michael-retro-Michael pathway for site-selective introduction of deuterium at the α-position of enals using D₂O as a deuterium source has been achieved. The mild, operationally simple protocol allows for high yielding and high level deuterium incorporation (up to 99%) for structurally diverse aromatic-derived enals and dienals.