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C-NH2 bond formation mediated by iridium complexes

AuthorsMena, Inmaculada ; Casado, Miguel A. ; Polo, Víctor; García-Orduña, P. ; Lahoz, Fernando J. ; Oro, Luis A.
KeywordsC-N formation
Amido transfer
N-H activation
Issue Date2014
CitationAngewandte Chemie International Edition 53(36): 9627-9631 (2014)
AbstractIn the presence of phosphanes (PR3), the amido-bridged trinuclear complex [{Ir(μ-NH2)(tfbb)}3] (tfbb=tetrafluorobenzobarrelene) transforms into mononuclear discrete compounds [Ir(1,2-η2-4-κ-C12H8F 4N)(PR3)3], which are the products of the C-N coupling between the amido moiety and a vinylic carbon of the diolefin. An alternative synthetic approach to these species involves the reaction of the 18-e- complex [Ir(Cl)(tfbb)(PMePh2)2] with gaseous ammonia and additional phosphane. DFT studies show that both transformations occur through nucleophilic attack. In the first case the amido moiety attacks a diolefin coordinated to a neighboring molecule following a bimolecular mechanism induced by the highly basic NH2 moiety; the second pathway involves a direct nucleophilic attack of ammonia to a coordinated tfbb molecule.
Publisher version (URL)http://dx.doi.org/10.1002/anie.201405237
Identifiersdoi: 10.1002/anie.201405237
issn: 1433-7851
e-issn: 1521-3773
Appears in Collections:(ISQCH) Artículos
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