Reductive Alkylation/Arylation of Arylcarbinols and Ketones with Organosilicon Compounds

Article abstract of DOI:10.1021/jo00132a027

Arylcarbinols react with certain organosilanes in the presence of boron trifluoride to yield hydrocarbons resulting from transfer of an R group from silicon to carbon.The transfer works well with aryl- and allylsilanes and fails with alkylsilanes.Allylation of ionizable carbinols is sometimes accompanied by cation-mediated oligomerization.This can be offset by converting the carbinols in question to their respective allyldimethylsilyl ethers followed by rearrangement of the ethers with BF3.While diaryl ketones are sluggishly bisallylated, the corresponding ketals undergo smooth bisallylation at 0 deg C with allytrimethylsilane/BF3/CH2Cl2.