Unexpected regioselectivity in the palladium‐catalyzed reaction of silacyclobutanes with aryl iodides

Abstract

Abstract The reaction of aryl iodides with 1,1‐diphenyl‐silacyclobutane in the presence of a catalytic amount of Pd(PPh 3 ) 4 affords unexpected ring‐opening adducts, 1‐ and 2‐propenyl(triaryl)‐silanes, in good yields. On the other hand, the PdCl 2 (PhCN) 2 ‐catalyzed reaction of 1,1‐diphenylsilacyclobutanes with aryl halides gives ­unexpected products, triarylsilanols, after ­hydrolysis in moderate yields. The catalysis involves the reaction of aryl–palladium intermediates with silacyclobutanes along with ­regioselective aryl–silicon bond formation. Copyright © 2001 John Wiley & Sons, Ltd.