PALLADIUM(II)-CATALYZED CONJUGATE ADDITION OF AROMATICS TO ALPHA,BETA-UNSATURATED KETONES AND ALDEHYDES WITH ARYLANTIMONY COMPOUNDS

Triarylstibines react with alpha,beta-unsaturated ketones and aldehyde s in acetic acid at room temperature in the presence of AgOAc and a ca talytic amount of Pd(OAc)(2) to afford the conjugate addition products (the formal hydroarylated compounds to an olefinic part) in good yiel ds. In contrast, diarylantimony chlorides, arylantimony dichlorides, a nd diphenylantimony acetate react with the enones and enals even in th e absence of AgOAc to afford the same products in higher yields compar ed with those from triarylstibines. These are new C-C bond-forming rea ctions using arylantimony(III) compounds in which the formation of a p alladium enolate or a trivalent antimony enolate is proposed as an int ermediate.