Conversion of Bromoalkenes into Alkynes by Wet Tetra-<i>n</i>-butylammonium Fluoride

Abstract

Tetra-n-butylammonium fluoride was found to be a mild and efficient base for the elimination reaction of bromoalkenes. Treatment of 1,1-dibromoalkenes, (Z)-1-bromoalkenes, and internal bromoalkenes with 5 equiv of TBAF x 3H2O in DMF yielded terminal and internal alkynes in high yields without undue regard to the presence of water.