Generation of Sulfonyl Radicals from Aryldiazonium Tetrafluoroborates and Sulfur Dioxide: The Synthesis of 3-Sulfonated Coumarins

被引：312
作者：
Zheng, Danqing [1 ]
Yu, Jiyao [2 ]
Wu, Jie [1 ,3 ]
机构：
[1] Fudan Univ, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China
[2] Georgia State Univ, Dept Chem, Ctr Diagnost & Therapeut, Atlanta, GA 30303 USA
[3] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 39期
基金：
中国国家自然科学基金;
关键词：
diazo compounds; heterocycles; radicals; sulfur; synthetic methods; PALLADIUM-CATALYZED AMINOSULFONYLATION; VINYL SULFONES; ALKYL-HALIDES; ONE-POT; 3-COMPONENT REACTION; MEDICINAL CHEMISTRY; N-AMINOSULFONAMIDES; BIOLOGICAL-ACTIVITY; SURROGATE DABSO; SULFINIC ACIDS;
D O I：
10.1002/anie.201607292
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A catalyst-free approach for the generation of sulfonyl radicals from aryldiazonium tetrafluoroborates in the presence of DABCO center dot(SO2)(2) is realized. The combination of aryldiazonium tetrafluoroborates, DABCO center dot(SO2)(2), and aryl propiolates affords 3-sulfonated coumarins in good to excellent yields. This tandem reaction process involves radical addition, spirocyclization, and 1,2-migration of esters. Additionally, the in situ diazotization of a number of anilines allows the directional synthesis of desired 3-sulfonated coumarins in a one-pot, two-step process.
引用
收藏
页码：11925 / 11929
页数：5
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