Selective Synthesis of Secondary and Tertiary Amines by Cp*Iridium-Catalyzed Multialkylation of Ammonium Salts with Alcohols
- 13 December 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (2), 181-184
- https://doi.org/10.1021/ol702522k
Abstract
The efficient selective synthesis of secondary and tertiary amines has been achieved by means of Cp*Ir-catalyzed multialkylation of ammonium salts with alcohols without solvent: the reactions of ammonium acetate with alcohols gave tertiary amines exclusively, while those of ammonium tetrafluoroborate afforded secondary amines selectively. Using this method, secondary 5- and 6-membered cyclic amines were synthesized from ammonium tetrafluoroborate and diols in one pot.Keywords
This publication has 14 references indexed in Scilit:
- Selective Palladium-Catalyzed Arylation of Ammonia: Synthesis of Anilines as Well as Symmetrical and Unsymmetrical Di- and TriarylaminesJournal of the American Chemical Society, 2007
- Palladium-Catalyzed Coupling of Ammonia and Lithium Amide with Aryl HalidesJournal of the American Chemical Society, 2006
- N-Alkylation of amines with alcohols catalyzed by a Cp*Ir complexTetrahedron Letters, 2003
- Catalytic Leuckart−Wallach-Type Reductive Amination of KetonesThe Journal of Organic Chemistry, 2002
- Synthesis of Primary Amines: First Homogeneously Catalyzed Reductive Amination with AmmoniaOrganic Letters, 2002
- pH-Dependent Transfer Hydrogenation, Reductive Amination, and Dehalogenation of Water-Soluble Carbonyl Compounds and Alkyl Halides Promoted by Cp*Ir ComplexesOrganometallics, 2001
- Synthesis of secondary aminesTetrahedron, 2001
- Amination of aryl halides using copper catalysisTetrahedron Letters, 2001
- Biphasic Catalyzed Telomerization of Butadiene and Ammonia: Kinetics and New Ligands for Regioselective ReactionsChemistry – A European Journal, 1999
- Transition metal and enzyme catalyzed reactions involving reactions with ammonia and aminesChemical Reviews, 1992