Simple One-Pot Preparation of Some Highly Electrophilic Haloacetylenes

Abstract

Preparation of some bis(trialkylstannyl)acetylenes from the corresponding trialkylstannyl chlorides was improved. The tin reagents interact with reactive acid chlorides and bromides to afford intermediate 1-acyl-2-trialkylstannylacetylenes in quantitative yields. The subsequent halogenation performed as a one-pot procedure gives the target 1-acyl-2-haloacetylenes in high yields and provides an effective recycling of the expensive starting trialkylstannyl chlorides.