The Synthesis of Benzimidazoles and Quinoxalines from Aromatic Diamines and Alcohols by Iridium-Catalyzed Acceptorless Dehydrogenative Alkylation

被引：150

作者：

Hille, Toni ^{[1
]}

Irrgang, Torsten ^{[1
]}

Kempe, Rhett ^{[1
]}

机构：

[1] Univ Bayreuth, Lehrstuhl Anorgan Chem 2, D-95440 Bayreuth, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 19期

关键词：

acceptorless dehydrogenation; alcohols; benzimidazoles; iridium; quinoxalines; ONE-POT SYNTHESIS; REUSABLE HETEROGENEOUS CATALYST; SOLVENT-FREE SYNTHESIS; 1,2-DISUBSTITUTED BENZIMIDAZOLES; O-PHENYLENEDIAMINES; FACILE SYNTHESIS; 2-SUBSTITUTED BENZIMIDAZOLES; REGIOSELECTIVE SYNTHESIS; 3-COMPONENT SYNTHESIS; EFFICIENT CATALYST;

D O I：

10.1002/chem.201400400

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Benzimidazoles and quinoxalines are important N-heteroaromatics with many applications in pharmaceutical and chemical industry. Here, the synthesis of both classes of compounds starting from aromatic diamines and alcohols (benzimidazoles) or diols (quinoxalines) is reported. The reactions proceed through acceptorless dehydrogenative condensation steps. Water and two equivalents of hydrogen are liberated in the course of the reactions. An Ir complex stabilized by the tridentate P boolean AND N boolean AND P ligand N-2,N-6-bis(di-isopropylphosphino)pyridine-2,6-diamine revealed the highest catalytic activity for both reactions.

引用

页码：5569 / 5572

页数：4

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