Direct β-alkylation of aldehydes via photoredox organocatalysis

Abstract

Direct β-alkylation of saturated aldehydes has been accomplished by synergistically combining photoredox catalysis and organocatalysis. Photon-induced enamine oxidation provides an activated β-enaminyl radical intermediate, which readily combines with a wide range of Michael acceptors to produce β-alkyl aldehydes in a highly efficient manner. Furthermore, this redox-neutral, atom-economical C-H functionalization protocol can be achieved both inter-and intramolecularly. Mechanistic studies by various spectroscopic methods suggest that a reductive quenching pathway is operable. © 2014 American Chemical Society.