Organophotoredox-Catalyzed Fluoroalkylation of Morita-Baylis-Hillman Adducts Using Quaternary Fluoroalkyl Alcohols as the Fluoroalkylating Reagents.

Abstract

Photoredox-enabled fluoroalkylation of MBH adducts using quaternary fluoroalkyl alcohols as the fluoroalkylating radical reagents is described. The facile protocol displays excellent functional group tolerance toward a series of synthetic allyl scaffolds containing fluoroalkyl groups under mild conditions. The alternative wavelength of visible light delivers the desired product with different yields and Z/E selectivities. A radical pathway involving an O-centered radical that induces β-scission to form the key fluoroalkyl radical is proposed in this transformation.