Rhodium-catalyzed reaction of aroyl chlorides with alkynes or alkenes in the presence of disilanes

Abstract

Internal alkynes effectively undergo aroylarylation, that is 1,2-addition of aroyl and aryl groups, on treatment with aroyl chlorides in the presence of a catalytic amount of [RhCl(cod)] 2 and PPh 3 using hexamethyldisilane as reducing agent to produce the corresponding 1,3-diaryl-2-propen-1-one derivatives in good yields. The reaction can also proceed using relatively reactive alkenes such as norbornenes in place of the alkynes. Similar treatment of a terminal alkyne, phenylacetylene, with aroyl chlorides brings about aroylsilylation to give 1-aryl-2-phenyl-3-trimethylsilyl-2-propene-1-ones.