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.
| Original language | English |
|---|---|
| Pages (from-to) | 1682-1685 |
| Number of pages | 4 |
| Journal | Journal of the American Chemical Society |
| Volume | 133 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - Feb 16 2011 |
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
Fingerprint Dive into the research topics of 'Synthesis of amides from esters and amines with liberation of H <sub>2</sub> under neutral conditions'. Together they form a unique fingerprint.
Cite this
Gnanaprakasam, B., & Milstein, D. (2011). Synthesis of amides from esters and amines with liberation of H 2 under neutral conditions. Journal of the American Chemical Society, 133(6), 1682-1685. https://doi.org/10.1021/ja109944n