The Reaction of Diphenyl(trimethylsilylmethyl)phosphine with Carbonyl Compounds in the Presence of Fluorides

Article abstract of DOI:10.1246/bcsj.64.708

Diphenyl(trimethylsilylmethyl)phosphine (1) was allowed to react with benzophenone in the presence of CsF in N,N-dimethylformamide to give a mixture of methyldiphenylphosphine (2), (2,2-diphenyl-2-trimethylsiloxyethyl)diphenylphosphine (3) and (2-hydroxy-2,2-diphenylethyl)diphenylphosphine (4) in good yield.The use of about 10 molpercent of CsF gave 3 with fairly good selectivity.The reaction with benzaldehyde gave a similar result, but only protodesilylation occurred in the reaction with enolizable carbonyl compounds.