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Chemoselective Oxidation by Electronically Tuned Nitroxyl Radical Catalysts
Author(s) -
Hamada Shohei,
Furuta Takumi,
Wada Yoshiyuki,
Kawabata Takeo
Publication year - 2013
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.201302261
Subject(s) - nitroxyl , catalysis , chemistry , alcohol oxidation , hydride , photochemistry , electron transfer , organic chemistry , combinatorial chemistry , hydrogen
Electronic tuning: Nitroxyl radical 1 is shown to be an efficient catalyst for the oxidation of secondary alcohols, and promotes oxidation through an oxoammonium species which is highly reactive because of the adjacent electron‐withdrawing ester groups. Chemoselective oxidation of benzylic alcohols in the presence of aliphatic alcohols is observed and is proposed to proceed by a rate‐determining hydride transfer.