Synthesis of amides from esters and amines with liberation of H2 under neutral conditions.
Efficient synthesis of amides directly from esters and amines is achieved under mild, neutral conditions with the liberation of molecular hydrogen. Both primary and secondary amines can be utilized. This unprecedented, general, environmentally benign reaction is homogeneously catalyzed under neutral conditions by a dearomatized ruthenium-pincer PNN complex and proceeds in toluene under an inert atmosphere with a high turnover number (up to 1000). PNP analogues do not catalyze this transformation, underlining the crucial importance of the amine arm of the pincer ligand. A mechanism is proposed involving metal-ligand cooperation via aromatization-dearomatization of the pyridine moiety and hemilability of the amine arm.
Department of Organic Chemistry, Weizmann Institute of Science, Rehovot 76100, Israel.
Boopathy
B
Gnanaprakasam
David
D
Milstein
D000577:Amides / Q000138:chemical synthesis*; D000588:Amines / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D004952:Esters; D055772:Green Chemistry Technology / Q000379:methods*; D006859:Hydrogen / Q000737:chemistry*
D000577:Amides; D000588:Amines; D004952:Esters; D006859:Hydrogen