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

09 November 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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.

Keywords

TBADT
Hydrogen Atom Transfer
Flow Chemistry
Allylation
Telescoped Synthesis
Late-Stage Functionalization

Supplementary materials

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Supporting Information
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Experimental details, reaction optimization and spectroscopic analysis
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