A metal-free approach to highly functionalized 3-substituted-3-arylbenzofuran-2(3H)-ones. (7th November 2022)

• Record Type: Journal Article
• Authors: Dhotare, Bhaskar B.; Kumar, Sahil; Wadawale, Amey; Nayak, Sandip K.; Kumar, Mukesh; Goswami, Dibakar
• Is Part Of: New journal of chemistry. Volume 46:Number 45(2022)
• Page Start: 21906
• Page End: 21910
• Publication Date: 2022-11-07
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/d2nj03404b
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : A novel approach for H2 SO4 -mediated dehydrative substitution of 3-hydroxy-3-phenylbenzofuran-2(3 H )-ones with electron-rich arenes/1, 3-diones/alcohols/thiols as nucleophiles is presented. Abstract : A novel metal-free approach to the synthesis of a variety of 3-substituted-3-arylbenzofuran-2(3 H )-ones is developed via H2 SO4 -mediated dehydrative substitution of 3-hydroxy-3-phenylbenzofuran-2(3 H )-ones with electron-rich arenes/1, 3-diones/alcohols/thiols as nucleophiles in moderate to good yields. Mechanistically, the substitution with the alkoxy group proceeds via a phenolic–hydroxyester intermediate, and forms the desired product via cascade dehydration–relactonization steps.