C-Alkylation of hydroxyarenes by Michael reaction

Abstract

Electron-rich hydroxyarenes undergo self-catalytic Michael reaction with the dicyclohexylammonium acrylate 1. The regiochemistry of this reaction is markedly dependent on structural features of the starting hydroxyarenes. While at 25 °C and in nonpolar solvents phenol and most of its monosubstituted derivatives are converted into the corresponding O-adducts, conjugate addition of disubstituted phenols and naphthols leads to the C-adducts exclusively. An analogous reaction pattern is observed with the dicyclohexylammonium acrylate 2 as the Michael acceptor.