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

Teruhiro Kawano; Ryo Watari; Yoshihito Kayaki; Takao Ikariya

doi:10.1055/s-0037-1611794

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(12): 2542-2547
DOI: 10.1055/s-0037-1611794

special topic

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

Teruhiro Kawano

^aDepartment of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1-E4-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan eMail: ykayaki@o.cc.titech.ac.jp

,

Ryo Watari

^bEnvironmental Chemistry Sector, Environmental Science Research Laboratory, Central Research Institute of Electric Power Industry, 1646 Abiko, Abiko-shi, Chiba 270-1194, Japan

,

Yoshihito Kayaki *

^aDepartment of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1-E4-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan eMail: ykayaki@o.cc.titech.ac.jp

,

Takao Ikariya

^aDepartment of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 2-12-1-E4-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan eMail: ykayaki@o.cc.titech.ac.jp

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Abstract

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Published as part of the Special Topic Ruthenium in Organic Synthesis

Abstract

Synthesis of a Cp*Ru complex bearing an NH₂-functionalized N-heterocyclic carbene (C–N^H) 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–N^H) complex showed a higher catalytic performance than the related Cp*RuCl(P–N^H) and Cp*RuCl(N–N^H) complexes. In the reaction of N-arylcarboxamides, the amine products were obtained in satisfactory yields under mild temperature conditions.

Key words

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

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