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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201506578
Subject(s) - regioselectivity , chemistry , alkyl , manganese , bond cleavage , catalysis , cleavage (geology) , oxidative addition , oxidative phosphorylation , medicinal chemistry , organic chemistry , combinatorial chemistry , stereochemistry , biology , biochemistry , fracture (geology) , paleontology
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.