Hypervalent Iodine Catalyzed Cascade C−H Functionalization: An Atom‐Economical Strategy to Access Diverse 2‐Substituted Benzothiazoles

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2025-01-10 DOI:10.1002/ejoc.202401043

Kotari Shakeena , Bokka Srinivas , Thammana Subha Sai Sriram , Leela Prasad Chamanthula , Kiran Indukuri , Muthyala Murali Krishna Kumar , Santhosh Kumar Alla

{"title":"Hypervalent Iodine Catalyzed Cascade C−H Functionalization: An Atom‐Economical Strategy to Access Diverse 2‐Substituted Benzothiazoles","authors":"Kotari Shakeena , Bokka Srinivas , Thammana Subha Sai Sriram , Leela Prasad Chamanthula , Kiran Indukuri , Muthyala Murali Krishna Kumar , Santhosh Kumar Alla","doi":"10.1002/ejoc.202401043","DOIUrl":null,"url":null,"abstract":"<div><div>A metal‐free 4,5‐difluoro‐2‐iodobenzoic acid catalyzed C−H functionalization strategy has been developed for the synthesis of 2‐(hetero)aryl benzothiazoles from aryl isothiocyanates and unfunctionalized arenes/thiophenes/furans at room temperature. The procedure entails one‐pot cascade carbon−carbon and carbon−sulfur bond formation facilitated by triflic acid, which serves as both a Brønsted acid and a ligand source at the in situ generated I(III) center. This process is atom‐economical and offers benefits over existing protocols for synthesizing benzothiazoles in terms of ease of use, eco‐friendliness, and not requiring the typical use of aryl aldehyde/carboxylic acid precursors. Mechanistic studies were carried out, and the synthetic utility of the protocol was demonstrated for the synthesis of the benzothiazole‐based antitumor drug GW‐610.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 2","pages":"Article e202401043"},"PeriodicalIF":2.5000,"publicationDate":"2025-01-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1434193X24008065","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

Abstract

A metal‐free 4,5‐difluoro‐2‐iodobenzoic acid catalyzed C−H functionalization strategy has been developed for the synthesis of 2‐(hetero)aryl benzothiazoles from aryl isothiocyanates and unfunctionalized arenes/thiophenes/furans at room temperature. The procedure entails one‐pot cascade carbon−carbon and carbon−sulfur bond formation facilitated by triflic acid, which serves as both a Brønsted acid and a ligand source at the in situ generated I(III) center. This process is atom‐economical and offers benefits over existing protocols for synthesizing benzothiazoles in terms of ease of use, eco‐friendliness, and not requiring the typical use of aryl aldehyde/carboxylic acid precursors. Mechanistic studies were carried out, and the synthetic utility of the protocol was demonstrated for the synthesis of the benzothiazole‐based antitumor drug GW‐610.

Abstract Image

查看原文本刊更多论文

高价碘催化级联 C-H 功能化：获得多种 2-取代苯并噻唑的原子经济学策略

本研究开发了一种无金属、4,5-二氟-2-碘苯甲酸催化的 C-H 功能化策略，用于在室温下从芳基异硫氰酸酯和未功能化的炔/噻吩/呋喃合成 2-（杂）芳基苯并噻唑。该过程需要在三氟甲磺酸的促进下进行单锅级联碳-碳键和碳-硫键的形成，三氟甲磺酸在原位生成的 I(III)中心既是勃朗斯特德酸，又是配体源。与现有的苯并噻唑合成方法相比，该方法具有原子经济性、易用性和生态友好性等优点，而且不需要通常使用的芳基醛/羧酸前体。研究人员进行了机理研究，并在合成苯并噻唑类抗肿瘤药物 GW-610 时证明了该方案的合成实用性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.