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. 2021 Jul 16;23(14):5425-5429.
doi: 10.1021/acs.orglett.1c01758. Epub 2021 Jun 30.

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

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

Yu Lu et al. Org Lett. .

Abstract

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.

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