4.8 Article

Direct C-H Allylation of Unactivated Alkanes by Cooperative W/Cu Photocatalysis

Journal

ORGANIC LETTERS
Volume 24, Issue 37, Pages 6874-6879

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02887

Keywords

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Funding

  1. European Research Council [ERC- CoG 863914-BECAME]
  2. Agencia Estatal de Investigacion [PID2020-118237RB-I00]
  3. Xunta de Galicia [ED431C 2018/04, ED431G 2019/03]
  4. European Regional Development Fund (ERDF)

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Here we report a photocatalytic methodology that enables the direct allylation of strong aliphatic C-H bonds with simple allylic chlorides. The method relies on the cooperative interaction of two metal catalysts, allowing for functionalization of a variety of chemical feedstocks and natural products under mild conditions in short reaction times.
Here we report a photocatalytic methodology that enables the direct allylation of strong aliphatic C-H bonds with simple allylic chlorides. The method relies on a cooperative interaction of two metal catalysts in which the decatungstate anion acts as a hydrogen-atom abstractor generating a nucleophilic carbon-centered radical that engages in an S(H)2 ' reaction with an activated allylic pi-olefin-copper complex. Because of this dual catalysis, the protocol allows for the functionalization of a range of chemical feedstocks and natural products under mild conditions in short reaction times.

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