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

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.

 

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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