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Oxyfunctionalization of the Remote C−H Bonds of Aliphatic Amines by Decatungstate Photocatalysis
Author(s) -
Schultz Danielle M.,
Lévesque François,
DiRocco Daniel A.,
Reibarkh Mikhail,
Ji Yining,
Joyce Leo A.,
Dropinski James F.,
Sheng Huaming,
Sherry Benjamin D.,
Davies Ian W.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201707537
Subject(s) - photocatalysis , chemistry , photochemistry , photoredox catalysis , organic chemistry , catalysis
Aliphatic amines, oxygenated at remote positions within the molecule, represent an important class of synthetic building blocks to which there are currently no direct means of access. Reported herein is an efficient and scalable solution that relies upon decatungstate photocatalysis under acidic conditions using either H 2 O 2 or O 2 as the terminal oxidant. By using these reaction conditions a series of simple and unbiased aliphatic amine starting materials can be oxidized to value‐added ketone products. Lastly, NMR spectroscopy using in situ LED‐irradiated samples was utilized to monitor the kinetics of the reaction, thus enabling direct translation of the reaction into flow.