Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides. Issue 18 (13th April 2021)

• Record Type: Journal Article
• Authors: Nguyen, Vu T.; Haug, Graham C.; Nguyen, Viet D.; Vuong, Ngan T. H.; Arman, Hadi D.; Larionov, Oleg V.
• Is Part Of: Chemical science. Volume 12:Issue 18(2021)
• Page Start: 6429
• Page End: 6436
• Publication Date: 2021-04-13
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1sc01389k
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Sulfonamides are now accessible directly from carboxylic acids by a one-step, tricomponent decarboxylative amidosulfonation that provides the missing link between the two key functionalities. Abstract : Sulfonamides feature prominently in organic synthesis, materials science and medicinal chemistry, where they play important roles as bioisosteric replacements of carboxylic acids and other carbonyls. Yet, a general synthetic platform for the direct conversion of carboxylic acids to a range of functionalized sulfonamides has remained elusive. Herein, we present a visible light-induced, dual catalytic platform that for the first time allows for a one-step access to sulfonamides and sulfonyl azides directly from carboxylic acids. The broad scope of the direct decarboxylative amidosulfonation (DDAS) platform is enabled by the efficient direct conversion of carboxylic acids to sulfinic acids that is catalyzed by acridine photocatalysts and interfaced with copper-catalyzed sulfur–nitrogen bond-forming cross-couplings with both electrophilic and nucleophilic reagents.