Tetrahedron p. 11043 - 11062 (1995)
Update date:2022-08-04
Topics:
Stoner, Eric J.
Cothron, Darlene A.
Balmer, Mary K.
Roden, Brian A.
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.
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