4.4 Article

Three-Component Chlorophosphinoylation of Alkenes via Anodically Coupled Electrolysis

Journal

SYNLETT
Volume 30, Issue 10, Pages 1199-1203

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1689934

Keywords

electrochemistry; electrocatalysis; anodically coupled electrolysis; alkene difunctionalization; radical addition; chlorination; phosphine oxide

Funding

  1. Cornell University (Division of Chemistry)
  2. National Science Foundation (NSF) [CHE-1751839]
  3. National Science Foundation [CHE-1531632]

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We report the development of an electrocatalytic protocol for the chlorophosphinoylation of simple alkenes. Driven by electricity and mediated by a Mn catalyst, the heterodifunctionalization reaction takes place with high efficiency and regioselectivity. Cyclic voltammetry data are consistent with a mechanistic scenario based on anodically coupled electrolysis in which the generation of two distinct radical intermediates occur simultaneously on the anode and are both mediated by the Mn catalyst.

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