Synthesis 2019; 51(12): 2542-2547
DOI: 10.1055/s-0037-1611794
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Teruhiro Kawano
a  Department 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
b  Environmental Chemistry Sector, Environmental Science Research Laboratory, Central Research Institute of Electric Power Industry, 1646 Abiko, Abiko-shi, Chiba 270-1194, Japan
,
a  Department 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
a  Department 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
› Author Affiliations
This study was financially supported by the Japan Society for the Promotion of Science (JSPS KAKENHI, Grant Numbers 26620143 and 24350079).
Further Information

Publication History

Received: 22 February 2019

Accepted after revision: 19 March 2019

Publication Date:
25 April 2019 (eFirst)

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–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 N-arylcarboxamides, the amine products were obtained in satisfactory yields under mild temperature conditions.

Supporting Information

 
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