Lewis Acid-Catalyzed trans-Carbosilylation of Simple Alkynes

摘要

Since the first carbometallation discovered by Ziegler and Baehr in 1927, a number of additions of organometallics to carbon-carbon multiple bonds have been reported. Unfortunately, however, carbosilylation still remained unexploited due to the lack of a method for activation of carbon-silicon bonds. We wish to report that allylsilylation of simple unactivated acetylenes 1 is catalyzed dramatically by Lewis acids such as EtAlCl_2 or AlCl_3 to give the corresponding trans-allylsilylated alkynes 2 in good to high yields (eq 1).