Synthesis of amides from esters and amines with liberation of H 2 under neutral conditions

Boopathy Gnanaprakasam, David Milstein

Research output: Contribution to journalArticle

185 Citations (Scopus)

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 languageEnglish
Pages (from-to)1682-1685
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number6
DOIs
Publication statusPublished - Feb 16 2011

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Amides
Amines
Esters
Ligands
Aromatization
Ruthenium
Toluene
Atmosphere
Pyridine
Hydrogen
Metals

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Synthesis of amides from esters and amines with liberation of H 2 under neutral conditions. / Gnanaprakasam, Boopathy; Milstein, David.

In: Journal of the American Chemical Society, Vol. 133, No. 6, 16.02.2011, p. 1682-1685.

Research output: Contribution to journalArticle

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