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Nitrous Oxide as a Hydrogen Acceptor for the Dehydrogenative Coupling of Alcohols
Author(s) -
Gianetti Thomas L.,
Annen Samuel P.,
SantisoQuis Gustavo,
Reiher Markus,
Driess Matthias,
Grützmacher Hansjörg
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.201509288
Subject(s) - rhodium , chemistry , olefin fiber , acceptor , catalysis , hydride , hydrogen , metal , ligand (biochemistry) , oxide , photochemistry , medicinal chemistry , oxygen , carboxylic acid , hydrogen bond , polymer chemistry , organic chemistry , molecule , biochemistry , physics , receptor , condensed matter physics
The oxidation of alcohols with N 2 O as the hydrogen acceptor was achieved with low catalyst loadings of a rhodium complex that features a cooperative bis(olefin)amido ligand under mild conditions. Two different methods enable the formation of either the corresponding carboxylic acid or the ester. N 2 and water are the only by‐products. Mechanistic studies supported by DFT calculations suggest that the oxygen atom of N 2 O is transferred to the metal center by insertion into the Rh−H bond of a rhodium amino hydride species, generating a rhodium hydroxy complex as a key intermediate.
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