One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums

Article abstract of DOI:10.1016/0022-328X(87)85117-3

The carbonylation of a THF solution of aryllithium (aryl = Ph, o-anisyl) in the presence of an alkyl bromide, RBr; at atmospheric pressure and -78 deg C, affords diarylalkylcarbinols in good yields.Alkyl chlorides do not react under similar experimental conditions.This feature makes the reaction particularly useful for the synthesisof alcohols functionalized in the alkyl chain through subsequent reactions of the diaryl(chloro)alkylcarbinols.The procedure can also be adapted to afford substituted cyclic ethers.If the reaction is carried out in the presence of dibromoalkanes, only one bromine atom reacts, affording diaryl(bromo)alkylcarbinols which are useful intermediates.With secondary and tertiary alkyl bromides diaryl alkyl ethers are obtained in variable yields.