4.8 Article

BI-OAc-Accelerated C3-H Alkylation of Quinoxalin-2(1H)-ones under Visible-Light Irradiation

Journal

ORGANIC LETTERS
Volume 22, Issue 15, Pages 5984-5989

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02080

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Funding

  1. National Natural Science Foundation of China [21971001, 21702001]
  2. Natural Science Foundation of Anhui Province [1808085MB47]
  3. Open fund for Discipline Construction, Institute of Physical Science and Information Technology, Anhui University
  4. Anhui University

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An efficient, photoredox-catalyst-free radical alkylation of quinoxalin-2(1H)-ones has been described. This reaction utilizes 4-alkyl-1,4-dihydropyridines (R-DHPs) as alkyl radical precursors and acetoxybenziodoxole (BI-OAc) as an electron acceptor to undergo single-electron transfer with photoexcited R-DHPs. The benign conditions allow for good compatibility in the scope of both quinoxalin-2(1H)-ones and R-DHPs. The synthetic value of the protocol was also demonstrated by the successful functionalization of natural products and drug-based complex molecules

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