Manganese-Catalyzed Oxidative Azidation of Cyclobutanols: Regiospecific Synthesis of Alkyl Azides by CC Bond Cleavage

A novel, manganese-catalyzed oxidative azidation of cyclobutanols is described. A wide range of primary, secondary, and tertiary alkyl azides were generated in synthetically useful yields and exclusive regioselectivity. Aside from linear alkyl azides, otherwise elusive medium-sized cyclic azides wer...

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Published inAngewandte Chemie International Edition Vol. 54; no. 43; p. 12692
Main Authors Ren, Rongguo, Zhao, Huijun, Huan, Leitao, Zhu, Chen
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 19.10.2015
EditionInternational ed. in English
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Summary:A novel, manganese-catalyzed oxidative azidation of cyclobutanols is described. A wide range of primary, secondary, and tertiary alkyl azides were generated in synthetically useful yields and exclusive regioselectivity. Aside from linear alkyl azides, otherwise elusive medium-sized cyclic azides were also readily prepared. Preliminary mechanistic studies reveal that the reaction likely proceeds by a radical-mediated CC bond cleavage/CN3 bond formation pathway.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201506578