Syntheses and Application of Aminated Benzimidazole Derivatives in Transfer Hydrogenation Reaction of Ketones

被引：3

作者：

Duan, Kai ^{[1
]}

Li, Xiaona ^{[1
]}

Li, Yunqing ^{[1
]}

Wang, Jiaxi ^{[1
]}

机构：

[1] Hebei Univ Technol, Sch Chem Engn, Tianjin 300130, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 32卷 / 07期

关键词：

amino acid; benzimidazole; N-alkylation; microwave; Ru(II) complex; ketone; transfer hydrogenation; ASYMMETRIC TRANSFER HYDROGENATION; COMPLEXES; ENANTIOSELECTIVITY; RACEMIZATION; CATALYSTS;

D O I：

10.6023/cjoc201203013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of alpha-amino-benzimidazole derivatives 1 similar to 5 were synthesized by reaction of alpha-amino acid with o-phenylenediamine under microwave irradiation. 1-(1H-Benzo[d]imidazol-2-yl)ethanamine (1) reacted with bromobutane forming mono-butyl, dibutyl and tributyl substituted benzimidazole 1a similar to 1d; and the N-alkylated derivatives 1i similar to 1g were synthesized by protection of amine group by Boc and then N-alkylation. The catalytic capability of the catalyst generated in situ from Ru(II) compound and obtained benzimidazole derivatives were evaluated in the transfer hydrogenation of ketones using iso-PrOH as hydrogen donor and solvent. The results revealed that catalyst generated in situ from RuCl2(PPh3)(3) and ligands had moderate to high activity. The catalyst system with a-amino-benzimidazole derivative containing NH2 group is the most active and the highest TOF (turnover frequency) was up to 40200 h(-1).

引用

页码：1247 / 1254

页数：8

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