Visible-light-driven electron donor–acceptor complex induced sulfonylation of diazonium salts with sulfinates

Abstract

This work reports an efficient sulfonylation enabled by visible-light-induced radical coupling reaction between phenyl/heterocyclic diazonium salts and sulfinates. Mechanistic experiments disclosed the formation of a versatile electron donor–acceptor (EDA) complex....

A general electron donor–acceptor complex enabled cascade cyclization of alkynes to access sulfur-containing heterocycles

“…Based on these results and literature reports, 9 a plausible mechanism was proposed. Initially, deprotonation of 4-methylbenzenesulfinic acid leads to an arylsulfinate anion, which combines with 2-alkynylthioanisole to form an EDA complex ( I ).…”

“…Given these factors and relying on booming EDA chemistry, only limited EDA methods have been accomplished for these cascade reactions. 9 In 2018, Miao and Wang disclosed a novel EDA complex generated from arylsulfinic acids and biaryl isocyanides, which was applied in a three-component reaction of arylsulfinic acids, alkynes, and biaryl isocyanides for the construction of C6-(vinyl sulfone) phenanthridines (Scheme 1b). 9 a Later, another excellent photo-induced oxidative cyclization of N -propargyl anilines with sulfinic acids for the synthesis of 3-sulfonated quinolines was reported by Chen and Li's group (Scheme 1c).…”

Synthesis of 1-perfluoroalkyl-3-heteroaryl bicyclo[1.1.1]pentanes via visible light-induced and metal-free perfluoroalkylation of [1.1.1]propellane

“…The UV-Vis absorption spectra indicated the formation of EDA complexes after the reaction of perfluorobutyl iodide 3a and DBU (Scheme 4a). 22 Although a solution of perfluorobutyl iodide 3a or DBU in DMSO/H 2 O = 10/1 showed no obvious absorbance in the visible-light region, a mixture of DBU and 3a exhibited a significant bathochromic shift. In addition, a solution of 3a or DBU in DMSO/H 2 O = 10/1 stayed colorless, while a mixture of perfluorobutyl iodide 3a in the presence of DBU changed to an intense yellow color.…”

Chloroaluminate Ionic Liquid Immobilized on Magnetic Nanoparticles as a Heterogeneous Lewis Acidic Catalyst for the Friedel–Crafts Sulfonylation of Aromatic Compounds

“…The identification and purity of all products reported were determined by 1 H-NMR, 13 C-NMR, and HRMS. The well-known compounds 3a [ 63 ], 3a′ [ 63 ], 3b [ 64 ], 3b′ [ 65 ], 3c [ 64 ], 3d [ 64 ], 3e [ 66 ], 3e′ [ 65 ], 3f [ 64 ], 3f′ [ 65 ], 3g [ 64 ], 3g′ [ 67 ], 3h [ 68 ], 3i [ 69 ], 3m [ 70 ], 3m′ [ 71 ], 3n [ 32 ], 3o [ 70 ], 3s [ 30 ], and 3u [ 62 ] were found to be compatible with the previous literature. The unknown products are described below ( Figure S2 ).…”