Copper-Catalyzed Aza-Benzyl Transfer Michael Addition via C-C Bond Cleavage

J Org Chem. 2023 Mar 17;88(6):3523-3531. doi: 10.1021/acs.joc.2c02740. Epub 2023 Feb 23.

Abstract

A non-noble Cu-catalyzed transfer aza-benzyl Michael addition via the C-C bond cleavage of aza-benzyl alcohols has been disclosed. The unstrained C(sp3)-C(sp3) bond of an alcohol was selectively cleaved. This aza-benzyl transfer strategy provides a selective and environmentally benign approach for the C-alkylation of α,β-unsaturated carbonyl compounds that employs readily available alcohols as carbon nucleophiles and is characterized by a wide range of substrates and good to excellent yields.