4.8 Article

Primary, Secondary, and Tertiary gamma-C(sp(3))-H Vinylation of Amides via Organic Photoredox-Catalyzed Hydrogen Atom Transfer

Journal

ORGANIC LETTERS
Volume 20, Issue 19, Pages 6255-6259

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02737

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Funding

  1. National Natural Science Foundation of China [21732003]
  2. National Key Research and Development Program of China [2018YFC0310900]
  3. Fundamental Research Funds for the Central Universities [020514380131, 020814380092]

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An efficient strategy for primary, secondary and tertiary aliphatic gamma-C(sp(3))-H vinylation of amides with alkenylboronic acids is reported. These reactions are catalyzed by visible-light organic photoredox agents. Regioselective gamma-C(sp(3))-H vinylation of amides is controlled by a 1,5-hydrogen atom transfer of an amidyl radical generated in situ.

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