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使用醇类通过结构明确的NNS-Mn配合物催化选择性合成C-3烷基化吲哚和双吲哚甲烷

Well-Defined NNS-Mn Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Using Alcohols.

作者信息

Mondal Avijit, Sharma Rahul, Dutta Bishal, Pal Debjyoti, Srimani Dipankar

机构信息

Department of Chemistry, Indian Institute of Technology-Guwahati, Kamrup, Assam 781039, India.

出版信息

J Org Chem. 2022 Mar 18;87(6):3989-4000. doi: 10.1021/acs.joc.1c02702. Epub 2022 Mar 8.

Abstract

Herein, we demonstrated Mn-catalyzed selective C-3 functionalization of indoles with alcohols. The developed catalyst can also furnish bis(indolyl)methanes from the same set of substrates under slightly modified reaction conditions. Mechanistic studies reveal that the C-3 functionalization of indoles is going via a borrowing hydrogen pathway. To highlight the practical utility, a diverse range of substrates including nine structurally important drug molecules are synthesized. Furthermore, we also introduced a one-pot cascade strategy for synthesizing C-3 functionalized indoles directly from 2-aminophenyl ethanol and alcohol.

摘要

在此,我们展示了锰催化吲哚与醇的选择性C-3官能化反应。在稍微改变的反应条件下,所开发的催化剂还能从同一组底物中制备双(吲哚基)甲烷。机理研究表明,吲哚的C-3官能化反应是通过借氢途径进行的。为突出其实用性,合成了包括9种结构重要的药物分子在内的多种底物。此外,我们还引入了一种一锅串联策略,可直接从2-氨基苯乙醇和醇合成C-3官能化吲哚。

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