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通过铱催化的无受体脱氢烷基化反应,由芳香族二胺和醇类合成苯并咪唑和喹喔啉。

The synthesis of benzimidazoles and quinoxalines from aromatic diamines and alcohols by iridium-catalyzed acceptorless dehydrogenative alkylation.

作者信息

Hille Toni, Irrgang Torsten, Kempe Rhett

机构信息

Lehrstuhl für Anorganische Chemie II, Universität Bayreuth, Universitätsstrasse 30, NW I, 95440 Bayreuth (Germany), Fax: (+49) 921552157.

出版信息

Chemistry. 2014 May 5;20(19):5569-72. doi: 10.1002/chem.201400400. Epub 2014 Apr 7.

DOI:10.1002/chem.201400400
PMID:24711248
Abstract

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^N^P ligand N(2) ,N(6) -bis(di-isopropylphosphino)pyridine-2,6-diamine revealed the highest catalytic activity for both reactions.

摘要

苯并咪唑和喹喔啉是重要的氮杂芳烃,在制药和化工行业有许多应用。本文报道了从芳族二胺和醇(苯并咪唑)或二醇(喹喔啉)出发合成这两类化合物的方法。反应通过无受体脱氢缩合步骤进行。反应过程中释放出水和两当量的氢气。由三齿P^N^P配体N(2),N(6)-双(二异丙基膦基)吡啶-2,6-二胺稳定的铱配合物对这两种反应均显示出最高的催化活性。

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