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Synlett
DOI: 10.1055/a-2550-1878
letter
Hydrogen Atom Transfer Reactions

Visible-Light-Induced Hydrogen-Atom-Transfer Catalysis for the Regioselective Hydroacylation of N-Sulfonylimine Esters with Aldehydes

Zhiyong Chi‡
a   Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. of China
,
Siyuan Huang‡
a   Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. of China
,
Guo Tang
a   Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. of China
b   State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830017 Xinjiang, P. R. of China
,
Qianyi Zhao
c   School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, P. R. of China
,
Lei Gong 
a   Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. of China
› Author AffiliationsWe thank the National Natural Science Foundation of China (grants nos. 22371237 and 22071209), the National Youth Talent Support Program, and the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University (No. 2024Y01).
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Abstract

The hydroacylation of unsaturated π-systems with aldehydes offers a direct and atom-economical route for introducing both a hydrogen atom and an acyl group into an organic molecule. Whereas hydroacylation reactions with alkanes and alkenes are well established, transformations involving imines have been much less successful. Existing approaches often favor C–C bond formation over C–N bond formation, due to the inherent properties of imines and acyl radicals. We present a photochemical approach that specifically targets N-sulfonylimine esters in combination with aldehydes. This reaction is facilitated by a decatungstate-salt-mediated double hydrogen-atom-transfer (HAT) activation that uniquely promotes the formation of C–N bonds under mild and simple conditions. Our method permits the efficient synthesis of a broad spectrum of distinctive N-sulfonyl N-carbonyl amide products with exclusive regioselectivity. We expect this streamlined method to expand the synthetic toolkit available for constructing complex nitrogen-containing compounds.

Key words

visible light - photocatalysis - hydrogen atom transfer - hydroacylation - imines - regioselectivity

Supporting Information



Publication History

Received: 11 February 2025

Accepted after revision: 03 March 2025

Accepted Manuscript online:
03 March 2025

Article published online:
10 April 2025

© 2025. Thieme. All rights reserved

Georg Thieme Verlag KG
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