Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides.

Vu T Nguyen,Hadi D Arman,Ngan T H Vuong,Graham C Haug,Viet D Nguyen,Oleg V Larionov

doi:10.1039/d1sc01389k

Vu T Nguyen, Hadi D Arman + Show 4 more

Open Access

https://doi.org/10.1039/d1sc01389k

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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.

Highlights

The sulfonamide group is one the most centrally important functionalities.[1]
VTN, VDN, and NTHV carried out the experiments and GCH performed the computational studies, in consultation with OVL
OVL, wrote the manuscript, and VTN, VDN, NTHV, and GCH contributed to writing the manuscript

Summary

Introduction

The sulfonamide group is one the most centrally important functionalities.[1]. In drug discovery, the sulfonamide group occupies a preeminent position, due to the favorable properties that include a pronounced electron withdrawing character, hydrolytic stability, polarity, hydrogen bonding ability, and resistance to reduction and oxidation. We have developed a visible light-induced photocatalytic amidosulfonation platform that enables the rst direct conversion of a wide range of carboxylic acids to aliphatic and aromatic sulfonamides, as well as sulfonyl azides in an adaptive tricomponent process with electrophilic and nucleophilic N-centered coupling partners.

Results

Conclusion