Litcius/Paper detail

Light-Promoted Nickel-Catalyzed C–O/C–N Coupling of Aryl Halides with Carboxylic Acids and Sulfonamides

Tiantian Zhao, Hao-Ni Qin, Peng‐Fei Xu

2023Organic Letters37 citationsDOI

Abstract

A general strategy for the construction of dual-functional carbon–heteroatom bonds has been developed via a light-promoted nickel catalytic system. Employing a simple NiBr 2 as the catalyst without any exogeneous ligands and photosensitizers, a variety of esters and sulfonamide N-arylation derivatives, including celecoxib- and glimepiride-derived sulfonamides, were readily accessed with high functional group tolerance and high efficiency. Moreover, the UV–vis absorption spectrum and free radical trapping experiments aimed at revealing the mechanism of the reaction are also presented.

Topics & Concepts

ChemistryArylCatalysisSulfonamideFunctional groupNickelHalideHeteroatomCombinatorial chemistryPhotochemistryMedicinal chemistryOrganic chemistryAlkylPolymerSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions