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铁(III)催化芳基异硫氰酸酯通过C-H官能化区域选择性合成富电子苯并噻唑

Iron(III)-Catalyzed Regioselective Synthesis of Electron-Rich Benzothiazoles from Aryl Isothiocyanates via C-H Functionalization.

作者信息

Srinivas Bokka, Shakeena Kotari, Kota Durgeswari Lakkavarapu, Abhinav Valeti, Eswar Pyla, Geetha Sravani Rongali, Sampath Pavan Kumar Anandam, Indukuri Kiran, Dhanaraju Kumpatla Ayyappa, Murali Krishna Kumar Muthyala, Alla Santhosh Kumar

机构信息

Department of Chemistry, GITAM School of Science, GITAM (Deemed to be University), Gandhi Nagar, Rushikonda, Visakhapatnam, Andhra Pradesh 530045, India.

Chemistry-Discovery Research Lab, Dextro Synthesis Private Limited, Hyderabad, Telangana 500090, India.

出版信息

J Org Chem. 2023 Apr 7;88(7):4458-4471. doi: 10.1021/acs.joc.2c03078. Epub 2023 Mar 13.

DOI:10.1021/acs.joc.2c03078
PMID:36912001
Abstract

We report herein a direct synthetic route for the preparation of 2-arylbenzothiazoles using aryl isothiocyanates and electron-rich arenes. The synthetic route involves triflic acid promoted addition of the arenes to aryl isothiocyanates followed by FeCl-catalyzed C-S bond formation via C-H functionalization. The approach provides the advantage of synthesis of benzothiazoles without the conventional use of aryl aldehyde/carboxylic acid precursors employing the less expensive iron(III) catalyst.

摘要

我们在此报道了一种使用芳基异硫氰酸酯和富电子芳烃制备2-芳基苯并噻唑的直接合成路线。该合成路线包括三氟甲磺酸促进芳烃与芳基异硫氰酸酯的加成,然后通过C-H官能化在氯化铁催化下形成C-S键。该方法具有无需传统使用芳基醛/羧酸前体且采用成本较低的铁(III)催化剂来合成苯并噻唑的优点。

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