Design and Applications of a SO2 Surrogate in Palladium-Catalyzed Direct Aminosulfonylation between Aryl Iodides and Amines

被引：57

作者：

Jia, Xiuwen ^{[1
,2
]}

Kramer, Soren ^{[3
]}

Skrydstrup, Troels ^{[4
,5
]}

Lian, Zhong ^{[1
,2
]}

机构：

[1] Sichuan Univ, West China Hosp, State Key Lab Biotherapy, Dept Dermatol, Chengdu 610041, Peoples R China

[2] Sichuan Univ, West China Hosp, Canc Ctr, Chengdu 610041, Peoples R China

[3] Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark

[4] Aarhus Univ, Carbon Dioxide Activat Ctr, Interdisciplinary Nanosci Ctr iNANO, Gustav Wieds Vej 14, DK-8000 Aarhus C, Denmark

[5] Aarhus Univ, Dept Chem, Gustav Wieds Vej 14, DK-8000 Aarhus C, Denmark

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 13期

基金：

新加坡国家研究基金会; 中国国家自然科学基金;

关键词：

aminosulfonylation; aryl halides; cross-couplings; SO2; surrogates; sulfonamides; SULFUR-DIOXIDE SURROGATE; SULFONYL FLUORIDES; BORONIC ACIDS; MULTICOMPONENT REACTION; 3-COMPONENT SYNTHESIS; SODIUM METABISULFITE; SULFONAMIDES; INSERTION; HALIDES; DABSO;

D O I：

10.1002/anie.202014111

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new SO2 surrogate is reported that is cheap, bench-stable, and can be accessed in just two steps from bulk chemicals. Essentially complete SO2 release is achieved in 5 minutes. Eight established sulfonylation reactions proceeded smoothly by ex situ formation of SO2 by utilizing a two-chamber system in combination with the SO2 surrogate. Furthermore, we report the first direct aminosulfonylation between aryl iodides and amines. Broad functional group tolerance is demonstrated, and the method is applicable to pharmaceutically relevant substrates, including heterocyclic substrates.

引用

页码：7353 / 7359

页数：7

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