Metal-free selective reduction of acid chlorides to aldehydes using 1-hydrosilatrane

Partial reductions of carboxylic acids and their derivatives to aldehydes

“…67 A metal-free selective reduction of aroyl chlorides (76) to aldehydes was realized by Adler and coworkers, using a caged commercially available and easy-to-handle 1-hydrosilatrane (78) as a reducing reagent (Scheme 23). 68 Other N-coordinated and -activated hydrosilanes suitable for such transformations were earlier reported in 1988. 36 In the presence of a nucleophilic tertiary amine such as N-methylpyrrolidine (NMP), the reduction proceeds rapidly at ambient temperature, and produces aldehydes in up to 55% yield.…”