Beyond Click-Chemistry: Transformation of Azides with Cyclopentadienyl Ruthenium Complexes

The cyclopentadienyl Ru complexes Cp*RuCl(cod) (cod = 1,5-cyclooctadiene), Cp*RuCl(PPh3)2, and [CpRuCl2]2 (Cp = η5-1-methoxy-2,4-di-tert-butyl-3-neopentylcyclopentadienyl) are able to catalyze the decomposition of benzyl azides to give 1,3,5-triphenyl-2,4-diazapenta-1,4-diene (“hydrobenzamide”), benzyl-benzylideneamine, and benzonitrile. Reactions with the catalyst precursor [CpRuCl2]2 are particularly fast and give hydrobenzamide with high selectivity. A similar coupling reaction is observed for other benzylic azides but not for (2-azidoethyl)benzene and ethyl-4-azidobutanoate. If the reactions are performed in the presence of water, benzylic azides are converted into aldehydes. Mononuclear tetrazene complexes are formed in stoichiometric reactions of [CpRuCl2]2 with benzyl azide and (2-azidoethyl)benzene.


Published in:
Organometallics, 30, 3412-3418
Year:
2011
Publisher:
American Chemical Society
ISSN:
0276-7333
Keywords:
Laboratories:


Note: The status of this file is: EPFL only


 Record created 2011-05-26, last modified 2018-03-17

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