4.8 Article

Intermolecular Atom Transfer Radical Addition to Olefins Mediated by Oxidative Quenching of Photoredox Catalysts

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 12, Pages 4160-4163

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja108560e

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Funding

  1. Boston University
  2. NIGMS [P50-GM067041]
  3. NSF [CHE-0619339, CHE-0443618]

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Atom transfer radical addition of haloalkanes and alpha-halocarbonyls to olefins is efficiently performed with the photocatalyst Ir[(dF(CF3)ppy)(2)(dtbbpy)]PF6. This protocol is characterized by excellent yields, mild conditions, low catalyst loading, and broad scope. In addition, the atom transfer protocol can be used to quickly and efficiently introduce vinyl trifluoromethyl groups to olefins and access 1,1-cyclopropane diesters.

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