The reaction between primary amines (RNH2) and diaryl diazomethanes (Ar2CN2) in the presence of catalytic amounts of the complex [RuCl(eta(5)-(CH5)-H-5)(PPh3)(2)] (1), in chloroform at 60 degreesC, generally affords mixtures of imines Ar2C=NR as main product and amines Ar2CHNHR. Whereas Ar2CHNHR are formed by the expected carbene insertion into the N-H bond of the substrate, the generation of Ar2C=NR is unprecedented. The carbene intermediate [RuCl( CAr2)(eta(5)-C5H5)(PPh3)] seems to be the key-species involved in the formation of both products.

[RuCl(η5-C5H5)(PPh3)2] as Catalyst in the Reaction of Primary Amines with Diaryl Diazoalkanes: Unexpected Formation of Imines

DEL ZOTTO, Alessandro;BARATTA, Walter;VERARDO, Giancarlo;RIGO, Pierluigi
2003

Abstract

The reaction between primary amines (RNH2) and diaryl diazomethanes (Ar2CN2) in the presence of catalytic amounts of the complex [RuCl(eta(5)-(CH5)-H-5)(PPh3)(2)] (1), in chloroform at 60 degreesC, generally affords mixtures of imines Ar2C=NR as main product and amines Ar2CHNHR. Whereas Ar2CHNHR are formed by the expected carbene insertion into the N-H bond of the substrate, the generation of Ar2C=NR is unprecedented. The carbene intermediate [RuCl( CAr2)(eta(5)-C5H5)(PPh3)] seems to be the key-species involved in the formation of both products.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11390/676936
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