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

Abstract

AbstractThe reaction of aryl iodides with 1,1‐diphenyl‐silacyclobutane in the presence of a catalytic amount of Pd(PPh3)4 affords unexpected ring‐opening adducts, 1‐ and 2‐propenyl(triaryl)‐silanes, in good yields. On the other hand, the PdCl2(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.