Alkyl formates as transfer hydroalkylation reagents and their use in the conversion of imines to alkylamines

Etienne Crochet (1) , Lucile Anthore-Dalion (1) , Thibault Cantat (1)

1 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)

Easily accessible via a simple esterification of alcohols with formic acid, alkyl formates are used as a novel class of transfer hydroalkylation reagents, CO2 acting as a traceless linker. As a proof-of-concept, their reactivity in the transfer hydroalkylation of imines is investigated, using a ruthenium-based catalyst and LiI as promoter to cleave the C−O σ–bond of the formate scaffold. Providing tertiary amines, the reaction displays a reverse and complementary regioselectivity compared to previously reported transfer hydroalkylation strategies.

Domains: Catalysis; Organic chemistry

Etienne Crochet, Lucile Anthore-Dalion, Thibault Cantat. Alkyl formates as transfer hydroalkylation reagents and their use in the conversion of imines to alkylamines. 2022. ⟨cea-03712544⟩