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通过碳-碘键活化实现2-芳基-2-吲唑的无催化剂光芳基化反应。

Catalyst-free photoarylation of 2-aryl-2-indazoles by carbon-iodine bond activation.

作者信息

Prasanna Ram, Banik Swarnayu, Ajay Chidrawar, Sridhar B, Mohapatra Debendra K, Subba Reddy B V

机构信息

Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad - 500007, India.

Academy of Scientific and Innovative Research (AcSIR), Ghaziabad - 201002, India.

出版信息

Org Biomol Chem. 2024 Jul 31;22(30):6129-6134. doi: 10.1039/d4ob00820k.

Abstract

A photocatalyst-free visible-light induced arylation of 2-aryl-2-indazoles with aryl iodides has been developed for the first time to produce 3,2-diaryl-2-indazoles in good to moderate yields. In this transformation, potassium -butoxide acts as an activator of the C-I bond and also as a scavenger of generated HI in the reaction. This method exhibits high functional group tolerance with a wide substrate scope and it has been successfully applied to the synthesis of liver X receptor agonists and also for fluorescent probes. This is the first report on the photoarylation of 2-arylindazoles at the C3-position with aryl iodides under catalyst-free conditions.

摘要

首次开发了一种无光催化剂的可见光诱导2-芳基-2-吲唑与芳基碘的芳基化反应,以中等至良好的产率生成3,2-二芳基-2-吲唑。在该转化反应中,叔丁醇钾作为C-I键的活化剂,同时也是反应中生成的HI的清除剂。该方法对官能团具有高耐受性,底物范围广泛,已成功应用于肝脏X受体激动剂的合成以及荧光探针的制备。这是关于在无催化剂条件下2-芳基吲唑在C3位与芳基碘进行光芳基化反应的首次报道。

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