EDA mediated S-N bond coupling of nitroarenes and sodium sulfinate salts

被引：31

作者：

Lasso, Juan D. D. ^{[1
]}

Castillo-Pazos, Durbis J. J. ^{[1
]}

Sim, Malcolm ^{[1
]}

Barroso-Flores, Joaquin ^{[2
]}

Li, Chao-Jun ^{[1
]}

机构：

[1] McGill Univ, FRQNT Ctr Green Chem & Catalysis, Dept Chem, 801 Sherbrooke St W, Montreal, PQ H3A 0B8, Canada

[2] UNAM, Ctr Conjunto Invest Quim Sustentable, Unidad San Cayetano, UAEM, Carretera Toluca-Atlacomulco Km 14-5, Toluca 50200, Estado De Mexic, Mexico

来源：

CHEMICAL SCIENCE | 2023年 / 14卷 / 03期

关键词：

REDUCTION; COMPLEXES; ACID; DINITROBENZENE; PHOTOREDUCTION; PROTONATION; AMINES;

D O I：

10.1039/d2sc06087f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Despite their long-known photochemical properties and their industrial value, the use of nitroarenes as a productive photochemical handle in organic synthesis has remained relatively unexplored. More specifically, the photochemical formation of nitrogen-sulfur bonds from nitroarenes remains to be demonstrated. Herein, we report the design and application of a sulfinate-nitroarene electron donor-acceptor (EDA) complex and its subsequent use in the first light mediated catalyst-free synthesis of N-hydroxy-sulfonamides. The presence of the EDA was assessed spectroscopically and studied via DFT and TD-DFT calculations. A total of 32 examples including both electron withdrawing and electron donating groups were synthesized under our oxygen- and water-tolerant conditions.

引用

页码：525 / 532

页数：8

共 34 条

[1] CHARGE-TRANSFER COMPLEXES OF PYRENE WITH DINITROBENZENE AND TRINITROBENZENE ACCEPTORS [J].