Amide synthesis from alcohols and amines by the extrusion of dihydrogen.
An environmentally friendly method for synthesis of amides is presented where a simple ruthenium catalyst mediates the direct coupling between an alcohol and an amine with the liberation of two molecules of dihydrogen. The active catalyst is generated in situ from an easily available ruthenium complex, an N-heterocyclic carbene and a phosphine. The reaction allows primary alcohols to be coupled with primary alkylamines to afford the corresponding secondary amides in good yields. The amide formation presumably proceeds through a catalytic cycle where the intermediate aldehyde and hemiaminal are both coordinated to the metal catalyst.
Nordstrøm
Lars Ulrik
LU
Center for Sustainable and Green Chemistry, Department of Chemistry, Building 201, Technical University of Denmark, 2800 Kgs. Lyngby, Denmark.
Vogt
Henning
H
Madsen
Robert
R
D000438:Alcohols / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry
D000438:Alcohols; D000577:Amides; D000588:Amines; D012428:Ruthenium; D006859:Hydrogen