Mild, regiospecific hydrocarboxylation of alkynes catalyzed by nickel cyanide under phase transfer conditions

Abstract

Phase transfer catalyzed reaction of alkynes (e.g., phenylacetylene) with carbon monoxide, aqueous base, toluene as the organic phase, and catalytic amounts of nickel cyanide as the metal catalyst and cetyltrimethylammonium bromide as the phase transfer agent, affords unsaturated acids (e.g., atropic acid) in reasonable yields. This regiospecific reaction occurs under mild conditions.