Reaction of pentaarylantimony with acid halide, aldehyde and ketone

Article abstract of DOI:10.1016/0022-328X(95)05793-O

Pentaarylantimony (pentaphenylantimony, penta-p-tolylantimony and penta-p-chlorophenylantimony) was found to be a mild arylation reagent. The arylation was chemoselective toward aromatic acid halides to give the corresponding aromatic ketones. No direct addition to ketone and acid anhydride occurred. Arylation reactions of aldehyde or ketone were promoted by the addition of Lewis acid. The nucleophilicities of aromatic antimony compounds depend on the number of antimony-aromatic carbon bonds.