The triple role of rongalite in aminosulfonylation of aryldiazonium tetrafluoroborates: synthesis of N-aminosulfonamides via a radical coupling reaction

A simple and convenient method for N-aminosulfonamide synthesis from the cross-coupling of aryldiazonium tetrafluoroborates and rongalite under metal-free, oxidant-free, and room-temperature conditions is reported. This method does not require an external amine source, with the aryldiazonium tetrafl...

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Published inChemical communications (Cambridge, England) Vol. 54; no. 55; pp. 7641 - 7644
Main Authors Wang, Miao, Tang, Bo-Cheng, Wang, Jun-Gang, Xiang, Jia-Chen, Guan, Ao-Yu, Huang, Ping-Ping, Guo, Wu-Yinzheng, Wu, Yan-Dong, Wu, An-Xin
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
Subjects
Aromatic compounds
Chemical reduction
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Coupling
Cross coupling
Physical Sciences
Reagents
Science & Technology
Sulfur dioxide
INSERTION
DABCO-CENTER-DOT(SO2)
REAGENTS
SULFUR-DIOXIDE
ONE-POT
SULFONAMIDES
GENERATION
DABSO
DERIVATIVES
FIXATION
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Summary:A simple and convenient method for N-aminosulfonamide synthesis from the cross-coupling of aryldiazonium tetrafluoroborates and rongalite under metal-free, oxidant-free, and room-temperature conditions is reported. This method does not require an external amine source, with the aryldiazonium tetrafluoroborates participating as both an aryl radical and a potential amine source in the transformation. Mechanistic studies revealed that rongalite could act as a radical initiator, a sulfur dioxide surrogate and a reducing reagent simultaneously in this reaction.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc03778g