4.8 Article

Synthesis of 3-Acylindoles by Visible-Light Induced Intramolecular Oxidative Cyclization of o-Alkynylated N,N-Dialkylamines

Journal

ORGANIC LETTERS
Volume 16, Issue 12, Pages 3264-3267

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol501276j

Keywords

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Funding

  1. National Natural Science Foundation of China [21202207, J1103305]
  2. Research Fund for Guangzhou Peal River New Star of Science and Technology [2013J2200017]
  3. Fundamental Research Funds for the Central Universities
  4. Program for Changjiang Scholars and Innovative Research Team in University of China [IRT1298]

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A visible-light photoredox synthesis of 3-acylindoles through intramolecular oxidative cyclization of o-alkynylated N,N-dialkylamines is developed. The reaction proceeds effectively under mild reaction conditions using air as the oxidant, and only water is generated as a side product. A plausible mechanism involving the addition of a-amino alkyl radicals to alkynes, followed by C-O bond formation, is proposed.

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