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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 08: 1493 - 1497

DOI: https://doi.org/10.6023/cjoc1202213

Articles

Synthesis and Application of N-Heterocyclic Carbene in Transfer Hydrogenation

  • Gao Yanxuan ,
  • Zhou Hongyong ,
  • Li Yunqing ,
  • Wang Jiaxi
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  • School of Chemical Engineering, Hebei University of Technology, Tianjin 300130

Received date: 2012-02-21

  Revised date: 2012-03-29

  Online published: 2012-04-10

Supported by

Project supported by the Natural Science Foundation of Hebei Province (No. B2011202087).

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Abstract

A series of pyridine substituted imidazoles L1～L5 have been synthesized via reaction of chloromethylpyridine with imidazole. The effects of base, ruthenium precursor and temperature on the activity of catalyst formed in situ of N-heterocyclic carbene ligands with Ru precursor in catalytic hydrogen transfer reaction of aniline with glycol were evaluated. The results showed that the reaction of aniline with glycol promoted by RuCl3·H2O/3-methyl-1(2-pyridinylmethyl)-imidazole iodide (L3)/KOH at 185℃ selectively produced 2-(phenylamino)ethanol with the TON (turnover number) of 2130. In addition, the catalytic properties of RuCl3·H2O/L3/KOH in reaction of aniline with butanol, cyclohexanol, iso-propanol and phenylmethanol were also investigated. Under promotion of catalyst, the aniline reacted with alcohol to produce imine and secondary amine. In addition, the ester was formed by self transfer hydrogenation of primary alcohol. The selectivity and product structures were depended on the structure of alcohol and the reaction conditions.

Key words： N-heterocyclic carbene; ruthenium; transfer hydrogenation; N-alkylation; pyridine; imidazole

Cite this article

Gao Yanxuan , Zhou Hongyong , Li Yunqing , Wang Jiaxi . Synthesis and Application of N-Heterocyclic Carbene in Transfer Hydrogenation[J]. Chinese Journal of Organic Chemistry, 2012 , 32(08) : 1493 -1497 . DOI: 10.6023/cjoc1202213

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