Organic Chemistry

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

Authors

Abstract

The late-stage introduction of allyl groups provides an opportunity to synthetic organic chemists for subsequent diversification, providing 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 reaction. This practical protocol enables the modular and scalable allylation of valuable building blocks and medicinally relevant molecules.

Content

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Supplementary material

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Supporting Information
Experimental details, reaction optimization and spectroscopic analysis