de.mpg.escidoc.pubman.appbase.FacesBean
English
 
Help Guide Disclaimer Contact us Login
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT

Released

Journal Article

Homogeneous Catalytic Hydrogenation of Amides to Amines

MPS-Authors
http://pubman.mpdl.mpg.de/cone/persons/resource/persons58749

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

Locator
There are no locators available
Fulltext (public)
There are no public fulltexts available
Supplementary Material (public)

chem_201204270_sm_miscellaneous_information.pdf
(Supplementary material), 3MB

Citation

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
Abstract
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.