Synthesis and Application of N-Heterocyclic Carbene in Transfer Hydrogenation

doi:10.6023/cjoc1202213

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (08): 1493-1497.DOI: 10.6023/cjoc1202213 Previous Articles Next Articles

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氮杂环卡宾的合成及在氢转移反应中的应用

高艳炫, 周宏勇, 李云庆, 王家喜

河北工业大学化工学院天津 300130

收稿日期:2012-02-21 修回日期:2012-03-29 发布日期:2012-04-10
通讯作者: 王家喜 E-mail:jwang252004@126.com
基金资助:
河北省自然科学基金(No. B2011202087)资助项目.

Synthesis and Application of N-Heterocyclic Carbene in Transfer Hydrogenation

Gao Yanxuan, Zhou Hongyong, Li Yunqing, Wang Jiaxi

School of Chemical Engineering, Hebei University of Technology, Tianjin 300130

Received:2012-02-21 Revised:2012-03-29 Published:2012-04-10
Supported by:
Project supported by the Natural Science Foundation of Hebei Province (No. B2011202087).

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

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Gao Yanxuan, Zhou Hongyong, Li Yunqing, Wang Jiaxi. Synthesis and Application of N-Heterocyclic Carbene in Transfer Hydrogenation[J]. Chin. J. Org. Chem., 2012, 32(08): 1493-1497.

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氮杂环卡宾的合成及在氢转移反应中的应用

Synthesis and Application of N-Heterocyclic Carbene in Transfer Hydrogenation

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