Ruthenium-Catalyzed Amination of Ketones

  • Author: ChemistryViews.org
  • Published: 25 January 2016
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Advanced Synthesis & Catalysis/Wiley-VCH
thumbnail image: Ruthenium-Catalyzed Amination of Ketones

Primary amines are an important target for synthesis, both as products and as intermediates, for example in fine chemicals and drug production. While alcohol amination is a well-developed process to generate primary amines, their synthesis using reductive amination of ketones or aldehydes still has issues such as low yields and selectivities. A common problem is the undesired hydrogenation of the ketone to the corresponding alcohol.


Thomas Schaub, BASF SE, Ludwigshafen, Germany, and colleagues have developed an efficient and highly selective reductive amination of acetophenone derivatives to primary amines, using ammonia and hydrogen, as well as a ruthenium-based catalyst. The process uses [Ru(CO)ClH(PPh3)3] as a precatalyst in combination with diphosphine ligands. The simple 1,2-bis(diphenylphosphino)ethane (dppe) showed the best performance. Al(OTf)3 was used as an acidic co-catalyst.


The team used their optimized protocol on a range of acetophenone derivatives. The reaction proceeded with high selectivity, good to excellent yields, and good functional group tolerance. The researchers ascribe the high selectivity to the aluminium triflate co-catalyst, presumably caused by imine activation.


 

Article Views: 2877

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


Magazine of Chemistry Europe (16 European Chemical Societies)published by Wiley-VCH