Synthesis of Amides from Esters and Amines with Liberation of H2 under Neutral Conditions
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- 19 January 2011
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 133 (6) , 1682-1685
- https://doi.org/10.1021/ja109944n
Abstract
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.This publication has 33 references indexed in Scilit:
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