Issue 24, 2022

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

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.

Graphical abstract: Modular allylation of C(sp3)–H bonds by combining decatungstate photocatalysis and HWE olefination in flow

Supplementary files

Article information

Article type
Edge Article
Submitted
18 Mar 2022
Accepted
28 May 2022
First published
31 May 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022,13, 7325-7331

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

L. Capaldo, S. Bonciolini, A. Pulcinella, M. Nuño and T. Noël, Chem. Sci., 2022, 13, 7325 DOI: 10.1039/D2SC01581A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements