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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.

SUBMITTER: Capaldo L

PROVIDER: S-EPMC9214841 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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

Capaldo Luca L Bonciolini Stefano S Pulcinella Antonio A Nuño Manuel M Noël Timothy T

Chemical science 20220531 24

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 p ...[more]

PMID: 35799818

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