Direct Amide Synthesis from Either Alcohols or Aldehydes with Amines: Activity of Ru(II) Hydride and Ru(0) Complexes
- 6 April 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 75 (9), 3002-3006
- https://doi.org/10.1021/jo100254g
Abstract
An in situ generated catalyst from readily available RuH2(PPh3)4, an N-heterocyclic carbene (NHC) precursor, NaH, and acetonitrile was developed. The catalyst showed high activity for the amide synthesis directly from either alcohols or aldehydes with amines. When a mixture of an alcohol and an aldehyde was reacted with an amine, both of the corresponding amides were obtained with good yields. Homogeneous Ru(0) complexes such as (η4-1,5-cyclooctadiene)(η6-1,3,5-cyclooctatriene)ruthenium [Ru(cod)(cot)] and Ru3(CO)12 were also active in the amidation of an alcohol or an aldehyde with the help of an in situ generated NHC ligand.This publication has 54 references indexed in Scilit:
- Direct Thionation and Selenation of Amides Using Elemental Sulfur and Selenium and Hydrochlorosilanes in the Presence of AminesOrganic Letters, 2009
- Heterobimetallic Lanthanide/Sodium Phenoxides: Efficient Catalysts for Amidation of Aldehydes with AminesThe Journal of Organic Chemistry, 2009
- [Ru(NHC)(xantphos)(CO)H2] complexes: intramolecular C–H activation and applications in C–C bond formationDalton Transactions, 2009
- Reduction of N-(alkoxy(aryl)methyl)benzamide Compounds by a Hantzsch Ester 1,4-Dihydropyridine Using Pd/C as a CatalystCatalysis Letters, 2008
- Enzyme-Like Chemoselective Acylation of Alcohols in the Presence of Amines Catalyzed by a Tetranuclear Zinc ClusterJournal of the American Chemical Society, 2008
- Cobalt−Rhodium Heterobimetallic Nanoparticle-Catalyzed Synthesis of α,β-Unsaturated Amides from Internal Alkynes, Amines, and Carbon MonoxideOrganic Letters, 2007
- Direct and Transfer Hydrogenation of Ketones and Imines with a Ruthenium N-Heterocyclic Carbene ComplexAdvanced Synthesis & Catalysis, 2005
- Inter- and intramolecular carbon-hydrogen bond forming and cleavage reactivity of two different types of poly(trimethylphosphine)ruthenium intermediatesJournal of the American Chemical Society, 1991
- A new synthetic method for the preparation of cyclo-olefin ruthenium complexesJ. Chem. Soc., Dalton Trans., 1980
- Some N-Alkyl N'-Aryl FuramidinesJournal of the American Chemical Society, 1940