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Journal Article

Homogeneous Catalytic Hydrogenation of Amides to Amines


Leitner,  Walter
Institut für Technische und Makromolekulare Chemie RWTH Aachen University;
Service Department Leitner (Technical Labs), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Coetzee, J., Dodds, D. L., Klankermayer, J., Brosinski, S., Leitner, W., Slawin, A. M. Z., et al. (2013). Homogeneous Catalytic Hydrogenation of Amides to Amines. Chemistry - A European Journal, 19(33), 11039-11050. doi:10.1002/chem.201204270.

Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-C9D8-8
Hydrogenation of amides in the presence of [Ru(acac)3] (acacH=2,4-pentanedione), triphos [1,1,1-tris- (diphenylphosphinomethyl)ethane] and methanesulfonic acid (MSA) produces secondary and tertiary amines with selectivities as high as 93 % provided that there is at least one aromatic ring on N. The system is also active for the synthesis of primary amines. In an attempt to probe the role of MSA and the mechanism of the reaction, a range of methanesulfonato complexes has been prepared from [Ru(acac)3], triphos and MSA, or from reactions of [RuX(OAc)(triphos)] (X=H or OAc) or [RuH2(CO)(triphos)] with MSA. Crystallographically characterised complexes include: [Ru(OAc-κ1O)2(H2O)(triphos)], [Ru(OAc-κ2O,O′)(CH3SO31O)(triphos)], [Ru(CH3SO31O)2(H2O)(triphos)] and [Ru2(μ-CH3SO3)3(triphos)2][CH3SO3], whereas other complexes, such as [Ru(OAc-κ1O)(OAc-κ2O,O′)(triphos)], [Ru(CH3SO31O)(CH3SO32O,O′)(triphos)], H[Ru(CH3SO31O)3(triphos)], [RuH(CH3SO31O)(CO)(triphos)] and [RuH(CH3SO32O,O′)(triphos)] have been characterised spectroscopically. The interactions between these various complexes and their relevance to the catalytic reactions are discussed.