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

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...

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Bibliographic Details
Published in:European journal of organic chemistry 2024-11
Main Authors: Shakeena, Kotari, Srinivas, Bokka, Sai Sriram, Thammana Subha, Prasad Chamanthula, Leela, Indukuri, Kiran, Krishna Kumar, Muthyala Murali, Kumar Alla, Santhosh
Format: Article
Language:English
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Summary: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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202401043