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Manganese‐Catalyzed Oxidative Azidation of Cyclobutanols: Regiospecific Synthesis of Alkyl Azides by CC Bond Cleavage
Author(s) -
Ren Rongguo,
Zhao Huijun,
Huan Leitao,
Zhu Chen
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201506578
Subject(s) - regioselectivity , chemistry , alkyl , manganese , bond cleavage , catalysis , cleavage (geology) , oxidative addition , primary (astronomy) , medicinal chemistry , organic chemistry , combinatorial chemistry , geotechnical engineering , fracture (geology) , engineering , physics , astronomy
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/CN 3 bond formation pathway.