Synlett 2025; 36(02): 166-170
DOI: 10.1055/s-0043-1763753
letter

Generation of Carbamoyl Radicals and 3,4-Dihydroquinolin-2(1H)-ones Enabled by Iron Photoredox Catalysis

Yanhua Fu
a   Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China
,
Chao Zhang
a   Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China
,
Tao Cai
b   College of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing 312000, P. R. of China
,
Gaofeng Feng
a   Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000, P. R. of China
› Institutsangaben

We are grateful for financial support by the National Natural Science Foundation of China (Grants Nos. 21676166 and 21302130).


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Abstract

A new protocol for accessing 3,4-dihydroquinolin-2(1H)-ones was established through a sequence of iron-catalyzed photoredox generation of carbamoyl radicals from oxamic acids, addition of the carbamoyl radicals to electron-deficient alkenes, intramolecular cyclization, and aromatization. The process is compatible with a variety of N-phenyloxamic acids and monosubstituted, 1,1-disubstituted, and trisubstituted electron-deficient alkenes. Employing cheap, readily available, and environmentally benign iron as the catalyst, the protocol provides an excellent alternative for synthesis of 3,4-dihydroquinolin-2(1H)-ones.

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Publikationsverlauf

Eingereicht: 21. März 2024

Angenommen nach Revision: 16. April 2024

Artikel online veröffentlicht:
16. Mai 2024

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