Benzylation via Tandem Grignard Reaction - Iodotrimethylsilane (TMSI) Mediated Reduction

Article abstract of DOI:10.1016/0040-4020(95)00659-V

A method has been developed which allows for the large scale preparation of biarylmethanes.This method involves the initial formation of biarylmethanols via reaction of aryl Grignards with carbonyl compounds followed by a subsequent reduction with iodotrimethylsilane (TMSI).A number of improvements over existing literature procedures are reported as well as previously unobserved dimerizations.Studies reveal that as few as 3 equiv of TMSI will give complete reduction in most cases where either of the substituents are not heteroaromatic.Mono-substituted alkanols react with TMSI to afford the corresponding iodides.A mechanistic study of the TMSI reduction is also reported.