Copper-catalyzed radical Heck type cyclization: a three-component reaction of DABCO center dot(SO2)(2), aryldiazonium tetrafluoroborates and dienes toward sulfonated benzo- seven-membered nitrogen heterocycles

A three-component reaction of the sulfur dioxide surrogate of DABCO(SO2)(2), aryldiazonium tetrafluoroborates and dienes has been developed, affording a series of sulfonated benzo- seven-membered nitrogen heterocycles in moderate to good yields. This procedure was triggered by the insertion of an in...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 5; no. 17; pp. 2547 - 2551
Main Authors Wang, Hepan, Wang, Bingbing, Sun, Song, Cheng, Jiang
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.09.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
INSERTION
SULFUR-DIOXIDE
RINGS
SULFONYLATION
BETA-KETO SULFONES
GENERATION
C-H FUNCTIONALIZATION
ALKENYLATION
ALKYL-HALIDES
MULTICOMPONENT REACTION
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Summary:A three-component reaction of the sulfur dioxide surrogate of DABCO(SO2)(2), aryldiazonium tetrafluoroborates and dienes has been developed, affording a series of sulfonated benzo- seven-membered nitrogen heterocycles in moderate to good yields. This procedure was triggered by the insertion of an in situ formed arylsulfonyl radical derived from DABCO(SO2)(2) and aryldiazonium tetrafluoroborates into electron-deficient vinyl, proceeding with a halogen-free radical Heck type reaction during cyclization.
ISSN:2052-4129
DOI:10.1039/c8qo00615f