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C−C Bond‐Forming Strategy by Manganese‐Catalyzed Oxidative Ring‐Opening Cyanation and Ethynylation of Cyclobutanol Derivatives
Author(s) -
Ren Rongguo,
Wu Zhen,
Xu Yan,
Zhu Chen
Publication year - 2016
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.201510973
Subject(s) - cyanation , ring (chemistry) , bond cleavage , chemistry , manganese , triple bond , catalysis , cleavage (geology) , oxidative phosphorylation , combinatorial chemistry , medicinal chemistry , stereochemistry , polymer chemistry , organic chemistry , double bond , materials science , composite material , fracture (geology) , biochemistry
A novel C−C bond‐forming strategy employing manganese‐catalyzed ring‐opening of cyclobutanol substrates, followed by cyanation or ethynylation, is described. A cyano C1 unit and ethynyl C2 unit are regiospecifically introduced to the γ‐position of ketones at room temperature, providing a mild yet powerful method for production of elusive aliphatic nitriles and alkynes. All transformations described are based on a common sequence: 1) oxidative ring‐opening of cyclobutanol substrates by C−C bond cleavage; 2) radical addition to triple bonds bearing an arylsulfonyl group; and 3) radical‐mediated C−S bond cleavage.