Photocatalysis Enables the Hydroamidation of Alkenes Using Sulfonyl Azides and Hantzsch Esters

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Benjamin List

Wencke Leinung

Fu R, Xu M, Wang Y, Wu X, *, Bao X. * Soochow University, Suzhou, P. R. of China
Organo-Photocatalytic Anti-Markovnikov Hydroamidation of Alkenes with Sulfonyl Azides: A Combined Experimental and Computational Study.

Angew. Chem. Int. Ed. 2024; e202406069
DOI: 10.1002/anie.202406069.

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Key words

photocatalysis - hydroamidation - sulfonyl azides - alkenes - anti-Markovnikov

Significance

Wu, Bao, and co-workers report a photocatalyzed hydroamidation of various alkenes using aryl sulfonyl azides and a Hantzsch ester. The corresponding anti-Markovnikov sulfonyl amides are obtained in moderate to very good yields. Extensive experimental and computational studies suggest that triplet-triplet energy transfer (EnT) and subsequent hydrogen atom transfer (HAT) events take place, providing the key amidyl radical.

Comment

Various photochemical strategies have been used to generate reactive species from organic azides for various amination reactions. These include the formation of free nitrene intermediates via energy transfer from a photoexcited catalyst or the generation of N-centered radicals via single electron transfer. The authors present another approach in which the key step involves a hydrogen atom transfer to generate a reactive amidyl radical.

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Publication History

Article published online:
14 June 2024

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

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