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.

Modular allylation of C(sp3)–H bonds by combining decatungstate photocatalysis and HWE olefination in flow / Capaldo, L; Bonciolini, S; Pulcinella, A; Nuño, M; Noël, T. - In: CHEMICAL SCIENCE. - ISSN 2041-6520. - 13:(2022), pp. 7325-7331. [10.1039/D2SC01581A]

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

Capaldo L;
2022-01-01

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.
2022
Modular allylation of C(sp3)–H bonds by combining decatungstate photocatalysis and HWE olefination in flow / Capaldo, L; Bonciolini, S; Pulcinella, A; Nuño, M; Noël, T. - In: CHEMICAL SCIENCE. - ISSN 2041-6520. - 13:(2022), pp. 7325-7331. [10.1039/D2SC01581A]
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2961121
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 24
  • ???jsp.display-item.citation.isi??? 24
social impact