Copper-catalyzed carbon–carbon bond cleavage of primary propargyl alcohols: β-carbon elimination of hemiaminal intermediates

Abstract

The copper-catalyzed cleavage of carbon–carbon bonds in primary propargyl alcohols under oxygen was investigated. This process involves the formation and fragmentation of hemiaminals from aldehydes (oxidized alcohols) and amines. This reaction mechanism was supported by the formation of N-formyl amines and GC experimental results.