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

Angewandte Chemie
Rongguo RenChen Zhu

Abstract

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 C-C bond cleavage/C-N3 bond formation pathway.

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Citations

Nov 17, 2015·Organic Letters·Xiaofei ZhangPingping Tang
Aug 10, 2016·The Journal of Organic Chemistry·Dongping WangChen Zhu
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Aug 11, 2021·The Journal of Organic Chemistry·Qing-Xin SunLi-Na Guo

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