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

Zheng Danqing | Zendy; Yu Jiyao | Zendy; Wu Jie | Zendy

Premium

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

Author(s) -

Zheng Danqing,

Yu Jiyao,

Wu Jie

Publication year - 2016

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201607292

Subject(s) - dabco , sulfonyl , chemistry , radical , tandem , aryl , catalysis , combinatorial chemistry , sulfur , sulfur dioxide , aryl radical , organic chemistry , photochemistry , materials science , alkyl , composite material

A catalyst‐free approach for the generation of sulfonyl radicals from aryldiazonium tetrafluoroborates in the presence of DABCO⋅(SO 2 ) 2 is realized. The combination of aryldiazonium tetrafluoroborates, DABCO⋅(SO 2 ) 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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research