Catalytic N-Alkylation of Amines Using Carboxylic Acids and Molecular Hydrogen
- 20 October 2015
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 137 (42), 13580-13587
- https://doi.org/10.1021/jacs.5b07994
Abstract
A convenient, practical and green N-alkylation of amines has been accomplished by applying readily available carboxylic acids in the presence of molecular hydrogen. Applying an in situ formed ruthenium/triphos complex and an organic acid as cocatalyst, a broad range of alkylated secondary and tertiary amines are obtained in good to excellent yields. This novel method is also successfully applied for the synthesis of unsymmetrically substituted N-methyl/alkyl anilines through a direct three-component coupling reaction of the corresponding amines, carboxylic acids, and CO2 as a C1 source.Keywords
Funding Information
- Bundesministerium für Bildung und Forschung
- Bundesland Mecklenburg-Vorpommern
This publication has 100 references indexed in Scilit:
- Green synthesis of formamides using the Natrolite zeolite as a natural, efficient and recyclable catalystJournal of Molecular Catalysis A: Chemical, 2013
- Ruthenium‐Catalyzed Direct Methylation of Primary and Secondary Aromatic Amines Using Carbon Dioxide and Molecular HydrogenAngewandte Chemie-International Edition, 2013
- A General Catalytic Methylation of Amines Using Carbon DioxideAngewandte Chemie-International Edition, 2013
- Development of New Hydrogenations of Imines and Benign Reductive Hydroaminations: Zinc Triflate as a CatalystChemSusChem, 2012
- The Catalytic Amination of AlcoholsChemCatChem, 2011
- Selective Homogeneous Hydrogenation of Biogenic Carboxylic Acids with [Ru(TriPhos)H]+: A Mechanistic StudyJournal of the American Chemical Society, 2011
- Catalytic Hydrogenation of Carboxamides and Esters by Well-Defined Cp*Ru Complexes Bearing a Protic Amine LigandJournal of the American Chemical Society, 2011
- Iridium‐Catalyzed Asymmetric Hydrogenation of IminesChemistry – A European Journal, 2010
- The Domino Multicomponent Allylation Reaction for the Stereoselective Synthesis of Homoallylic AlcoholsAccounts of Chemical Research, 2009
- Ruthenium-catalyzed Hydrogenation of Acids to AlcoholsJournal of the American Chemical Society, 1955