2006 Volume 54 Issue 5 Pages 699-702
Palladium-catalyzed carbonylative cross-coupling reaction of ethynylstibane (Ph⌯SbPh2) and aryl iodides (Ar-I) is described. The reaction of the stibanes and the halides under 1 atm of carbon monoxide in N,N-dimethylacetamide using a combination of 5 mol% Pd(OAc)2 and 4 equivalents (20 mol%) of PPh3 brought about carbonylative cross-coupling reaction to afford arylethynylketones [ArC(O)⌯Ph] in good yields along with a small amount of directly coupled products, aryl acetylens (Ar⌯Ph). Formation of the side product was completely suppressed by conducting the reaction under high CO pressure (20 atm) conditions. The present method provides a variety of carbonylated products in good yield even with electron-deficient aryl iodides which usually give inferior results due to their tendency to undergo decarbonylation in the cross-coupling reaction of ethynylstibanes and acyl halides.