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

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 NiBr2 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.

Photoexcited NiII–Aryl Complex-Mediated Giese Reaction of Aryl Bromides

“…Mechanistic studies suggest that the Ni I –halide complex is formed in situ and subsequently engages in a Ni I –Ni III catalytic cycle. Despite these pioneering works achieved, the versatility and synthetic utilizations of nickel catalysts upon photoexcitation still remain underexplored …”

Nickel-Catalyzed Selective C–H Cyanation via Aromatic Thianthrenium Salts

“…13 N-(4-Cyanophenyl)-4-methylbenzenesulfonamide (11b). 26 The crude product was purified by chromatography on silica gel eluting with hexane/ethyl acetate [(v/v, 1/1)] to afford 20.15 mg (74%) of 11b as a white solid. 1 H NMR (400 MHz, DMSO) δ: 11.17 (s, 1H), 7.77−7.71 (m, 2H), 7.70−7.76 (m, 2H), 7.36 (d, J = 8.2 Hz, 2H), 7.33−7.22 (m, 2H), 2.34 (s, 3H).…”

N‐Heteroarylation of Sulfonamides: An Overview

“…Through the use of a light‐promoted nickel catalytic system, a practical method for constructing dual‐functional carbon‐heteroatom bonds was devised recently by Zhao et al [50] . in 2023.…”

“…Through the use of a light-promoted nickel catalytic system, a practical method for constructing dual-functional carbon-heteroatom bonds was devised recently by Zhao et al [50] in 2023. Without the use of exogenous ligands or photosensitizers, a range of esters and sulfonamide N-arylation derivatives, such as those produced from celecoxib and glimepiride, were described.…”