Modular allylation of C(sp3)-H bonds by combining decatungstate photocatalysis and HWE olefination in flow

Chem Sci. 2022 May 31;13(24):7325-7331. doi: 10.1039/d2sc01581a. eCollection 2022 Jun 22.

Abstract

The late-stage introduction of allyl groups provides an opportunity to synthetic organic chemists for subsequent diversification, furnishing a rapid access to new chemical space. Here, we report the development of a modular synthetic sequence for the allylation of strong aliphatic C(sp3)-H bonds. Our sequence features the merger of two distinct steps to accomplish this goal, including a photocatalytic Hydrogen Atom Transfer and an ensuing Horner-Wadsworth-Emmons (HWE) reaction. This practical protocol enables the modular and scalable allylation of valuable building blocks and has been applied to structurally complex molecules.