4.5 Article

Catalytic Hydrogenation of Carboxamides with a Bifunctional Cp*Ru Catalyst Bearing an Imidazol-2-ylidene with a Protic Aminoethyl Side Chain

Journal

SYNTHESIS-STUTTGART
Volume 51, Issue 12, Pages 2542-2547

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1611794

Keywords

ruthenium; hydrogenation; amides; amines; alcohols; N-heterocyclic carbenes

Funding

  1. Japan Society for the Promotion of Science (JSPS KAKENHI) [26620143, 24350079]
  2. Grants-in-Aid for Scientific Research [26620143] Funding Source: KAKEN

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Synthesis of a Cp* Ru complex bearing an NH2-functionalized N-heterocyclic carbene (C-NH) was achieved by treatment of Cp* RuBr( isoprene) with an equimolar amount of a silver complex, which was generated from Ag2O and 1-(2-aminoethyl)-3-methylimidazolium bromide, in CH3CN at room temperature. The new Cp* RuBr(C-NH) complex showed a higher catalytic performance than the related Cp* RuCl( P-NH) and Cp* RuCl(N-NH) complexes. In the reaction of Narylcarboxamides, the amine products were obtained in satisfactory yields under mild temperature conditions.

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