Manganese-mediated/-catalyzed oxidative carboazidation of acrylamides

Manganese-mediated/-catalyzed oxidative carboazidation of acrylamides was developed for the synthesis of various azido oxindoles in 32% to 99% yields. tert-Butyl peroxybenzoate (TBPB) was used as an oxidant for the Mn-catalyzed method. And a Mn(II)/Mn(IV)/Mn(III) catalysis cycle via a stepwise or co...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 4; no. 8; pp. 1555 - 1560
Main Authors Zhao, Danwei, Kang, Kai, Wan, Wen, Jiang, Haizhen, Deng, Hongmei, Chen, Yunrong, Hao, Jian
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.08.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
COPPER PHOTOREDOX CATALYST
ACTIVATED ALKENES
HYPERVALENT IODINE
C-H AZIDATION
BOND-FORMING REACTIONS
ASYMMETRIC EPOXIDATION
OLEFINS
SUPRAMOLECULAR CLICK CHEMISTRY
GRIGNARD-REAGENTS
ALKYL AZIDES
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Summary:Manganese-mediated/-catalyzed oxidative carboazidation of acrylamides was developed for the synthesis of various azido oxindoles in 32% to 99% yields. tert-Butyl peroxybenzoate (TBPB) was used as an oxidant for the Mn-catalyzed method. And a Mn(II)/Mn(IV)/Mn(III) catalysis cycle via a stepwise or concerted regeneration of high-valent manganese was proposed for this protocol. This reaction system exhibits great functional group tolerance.
ISSN:2052-4129
DOI:10.1039/c7qo00217c