Deaminoarylation of sulfonamides

In 2019, Fier and Maloney et al. provided a sulfonylation functionalization modification under NHC-catalyzed deamination.

Recently, Luo Yong's group at Sun Yat-sen University Shenzhen Campus has modified the sulfonamide substrate to achieve a new method of photocatalytic S-N bond breaking to obtain sulfonyl radicals.

The single electron transfer radicalization is aided by such similar modifications, and previously the group of Shouyun Yu at Nanjing University also achieved the breakage of the N-O bond by such modifications to obtain nitrogen radicals, completing the nitrogen radical-initiated functionalization modification process-Org. Lett. 2017, 19, 2909.

Based on the previous work, Luo Yong's group at the Shenzhen Campus of Sun Yat-sen University has successfully realized a new method of photocatalytic cleavage of sulfonyl radicals by naked sulfonamides.

The Rovis group achieved aldehyde-induced N-C bond breakage to achieve deamination.

Two possible mechanisms are seen in the mechanism study, one EDA, raw material both in the action of alkali to get EDA complex, followed by the process of aromatization modification of sulfone under the action of light; the second in the action of photosensitizer to achieve the process of single electron transfer to get sulfonyl radicals, while aryl boronic acid compounds to achieve electron transfer to get aryl radicals, followed by free radical coupling process.