Donor–Acceptor Complex Enables Cascade Radical Cyclization of N‑Arylacrylamides with Katritzky Salts

Cascade radical cyclization of N-arylacrylamides is an attractive method to prepare 3,3-disubstituted oxindoles. As the reported methods often require additives and/or photocatalysts, we herein report an additive- and photocatalyst-free deaminative strategy for their synthesis under mild conditions,...

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Bibliographic Details
Published in:Organic letters 2021-07, Vol.23 (14), p.5425-5429
Main Authors: Lu, Yu, Fang, Chang-Zhen, Liu, Qiang, Li, Bao-Lin, Wang, Zhi-Xiang, Chen, Xiang-Yu
Format: Article
Language:English
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Summary:Cascade radical cyclization of N-arylacrylamides is an attractive method to prepare 3,3-disubstituted oxindoles. As the reported methods often require additives and/or photocatalysts, we herein report an additive- and photocatalyst-free deaminative strategy for their synthesis under mild conditions, enabled by photoactivation of an electron donor–acceptor (EDA) complex. DFT studies indicated that the involvement of an explicit xylene solvent molecule can greatly enhance the photoactivity of the EDA complex between N-arylacrylamides and Katritzky salts.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01758