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

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 m...

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Bibliographic Details
Published in:Organic letters 2014-06, Vol.16 (12), p.3264-3267
Main Authors: Zhang, Ping, Xiao, Tiebo, Xiong, Shengwei, Dong, Xichang, Zhou, Lei
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Amines - chemistry
Catalysis
Cyclization
Indoles - chemical synthesis
Indoles - chemistry
Light
Molecular Structure
Oxidation-Reduction
Water - chemistry
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Summary: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 α-amino alkyl radicals to alkynes, followed by C–O bond formation, is proposed.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol501276j