Copper-catalyzed 1,2-Borylacylation of 1,3-Enynes: synthesis of β-Alkynyl ketones

Abstract

A copper catalyzed 1,2-borylacylation of 1,3-enynes with B₂pin₂ and acid chlorides has been developed. Using readily available 1,3-enynes, B₂pin₂ and acid chlorides as substrates, a range of highly functionalized α,α-disubstituted β-alkynyl ketones were readily prepared under mild conditions in moderate to good yields. The borylacylated products can be easily derivatized to give several valuable structures. Notably, treatment of the products with NaBO₃·4H₂O provided 1,2-allenyl ketones, which is proposed to proceed via a retro-aldol process of the corresponding homopropargyl alcohols.