Deaminative Addition of Alkylpyridinium Salt to Aldehyde

Org Lett. 2023 Jul 7;25(26):4934-4939. doi: 10.1021/acs.orglett.3c01724. Epub 2023 Jun 26.

Abstract

Here we show that a primary amine can engage in the nucleophilic addition to an aldehyde to synthesize an alcohol following preactivation of the amine. The enabling reagent for this radical-polar crossover process is CrCl2. This reaction is selective for aldehydes and compatible with numerous functional groups, which are not tolerated under classical Grignard-type conditions. Complementary to the well-established imine synthesis, this deaminative alcohol synthesis can broadly expand the chemical space constructed by aldehydes and amines.