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一锅法吡咯-醛缩合反应作为通用自组装过程的视角。

A perspective of one-pot pyrrole-aldehyde condensations as versatile self-assembly processes.

作者信息

Ghosh Abhik

机构信息

Department of Chemistry, University of Tromsø, 9037 Tromsø, Norway.

出版信息

Angew Chem Int Ed Engl. 2004 Apr 2;43(15):1918-31. doi: 10.1002/anie.200201603.

DOI:10.1002/anie.200201603
PMID:15065269
Abstract

Regarded as the classic one-pot synthetic route to symmetrical porphyrins for well over half a century, pyrrole-aldehyde cyclocondensations have yielded a cornucopia of nonporphyrin macrocycles, such as N-confused porphyrins, corroles, sapphyrins, and expanded porphyrins, and have thus emerged as versatile self-assembly processes. A highlight in this field is the remarkably general one-pot corrole synthesis. The manifold of intermediates generated in the anaerobic phase of a Lindsey-type synthesis have been viewed as a dynamic covalent self-assembly system. This raises the possibility that the addition of a suitable host may alter the equilibrium concentrations of these intermediates by molecular recognition and related phenomena and thus determine the major product formed after oxidative quenching.

摘要

半个多世纪以来,吡咯 - 醛环缩合反应一直被视为合成对称卟啉的经典一锅法合成路线,该反应产生了大量的非卟啉大环化合物,如N-杂卟啉、corrole、蓝宝石卟啉和扩展卟啉,因此已成为通用的自组装过程。该领域的一个亮点是非常普遍的一锅法合成corrole。林赛型合成厌氧阶段产生的多种中间体被视为一个动态共价自组装系统。这就增加了一种可能性,即加入合适的主体可能通过分子识别和相关现象改变这些中间体的平衡浓度,从而决定氧化猝灭后形成的主要产物。

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