Generation of sulfonated 1-isoindolinones through a multicomponent reaction with the insertion of sulfur dioxide

A four-component reaction of 2-vinylbenzoic acids, aryldiazonium tetrafluoroborates, the sulfur dioxide surrogate DABCO·(SO 2 ) 2 , and nitriles under photocatalysis in the presence of visible light is developed. This multicomponent reaction works efficiently, promoted by BF 3 ·OEt 2 with the insert...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018-04, Vol.54 (31), p.3891-3894
Main Authors: Zhang, Jun, Zhang, Feng, Lai, Lifang, Cheng, Jiang, Sun, Jiangtao, Wu, Jie
Format: Article
Language:English
Subjects:
Insertion
Lewis acid
Nitriles
Photocatalysis
Sulfur
Sulfur dioxide
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Summary:A four-component reaction of 2-vinylbenzoic acids, aryldiazonium tetrafluoroborates, the sulfur dioxide surrogate DABCO·(SO 2 ) 2 , and nitriles under photocatalysis in the presence of visible light is developed. This multicomponent reaction works efficiently, promoted by BF 3 ·OEt 2 with the insertion of sulfur dioxide under mild conditions, leading to sulfonated 1-isoindolinones in moderate to good yields. This route is highly selective, and several competitive pathways are not observed under these conditions. A possible mechanism involving photocatalysis and a Lewis acid is proposed. A four-component reaction of 2-vinylbenzoic acids, aryldiazonium tetrafluoroborates, sulfur dioxide, and nitriles under photocatalysis in the presence of visible light is developed, leading to sulfonated 1-isoindolinones in moderate to good yields.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc01124a