Modified Sonogashira-style coupling reaction with incorporation of carbon monoxide

Brikho, Yousif, Alethea Fei, Witold Fuchs, Nadine Husseini, Kevin Suiter, and Matthew Mio

Inclusion of carbon monoxide at atmospheric pressure in a modified cross-coupling reaction has resulted in pseudo-Sonogashira products where carbonyls have been added between aryl and acetylene functional groups. Removal of a terminal silylacetylene protecting group in situ allows for a one-pot transformation. Crucial to the reaction conditions are dual nitrogenous bases (ammonia and amidines) and water as a solvent. Copper(I) iodide is also required for the transformation, which has been shown to be applicable to a number of differently-substituted aryl halide starting materials, as well as alkyl- and aryl-acetylenes.