Regioselective Propargylation of Carbonyl Compounds with (3-Bromoprop-1-ynyl)trimethylsilane Promoted by Reactive Barium

Abstract

A Barbier-type propargylation of aldehydes with (3-bromoprop-1-ynyl)trimethylsilane has been achieved using reactive barium as a low-valent metal in THF. This process is effective also for obtaining the desired homopropargylic alcohols in high yields from the corresponding ketones including enolizable ketones such as cyclopent-2-enone.

Key words

barium - propargylation - aldehydes - regioselectivity - ketones

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