Synthesis of (E)-2-(1-(methoxyimino)ethyl)-2-phenylbenzofuran-3(2H)-ones from (E)-1-(benzofuran-2-yl)ethan-1-one O-methyl oximes and iodobenzenes via a palladium-catalyzed dearomative arylation/oxidation reaction

Wen-Jing Zhu; Xiao Yu; Hong-Yan Liu; Yi Liu; Jin-Bo Zhao; Peng-Fei Zhang; Cheng-Cai Xia; Fu-Rong Li

doi:10.1039/D3OB00772C

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Synthesis of (E)-2-(1-(methoxyimino)ethyl)-2-phenylbenzofuran-3(2H)-ones from (E)-1-(benzofuran-2-yl)ethan-1-one O-methyl oximes and iodobenzenes via a palladium-catalyzed dearomative arylation/oxidation reaction†

Wen-Jing Zhu,^a Xiao Yu,^a Hong-Yan Liu,^a Yi Liu,^a Jin-Bo Zhao,^a Peng-Fei Zhang,

^b Cheng-Cai Xia

*^a and Fu-Rong Li*^a

Author affiliations

* Corresponding authors

^a School of Pharmacy College, Institute of Pharmacology, Shandong First Medical University & Shandong Academy of Medical Sciences, Tai'an, China
E-mail: xiachc@163.com

^b College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, China

Abstract

A new method has been successfully developed that offers a facile and reliable approach for synthesizing (E)-2-(1-(methoxyimino)ethyl)-2-phenylbenzofuran-3(2H)-one, providing 28 compounds. This optimized process enables efficient preparation of a wide range of compounds using readily available (E)-1-(benzofuran-2-yl)ethan-1-one O-methyl oxime and iodobenzene, and provides alternative ideas for the structural modification of benzofuran ketones.

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Article information

DOI: https://doi.org/10.1039/D3OB00772C
Article type: Communication
Submitted: 17 May 2023
Accepted: 19 Jul 2023
First published: 26 Jul 2023

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Org. Biomol. Chem., 2023,21, 6307-6311

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Synthesis of (E)-2-(1-(methoxyimino)ethyl)-2-phenylbenzofuran-3(2H)-ones from (E)-1-(benzofuran-2-yl)ethan-1-one O-methyl oximes and iodobenzenes via a palladium-catalyzed dearomative arylation/oxidation reaction

W. Zhu, X. Yu, H. Liu, Y. Liu, J. Zhao, P. Zhang, C. Xia and F. Li, Org. Biomol. Chem., 2023, 21, 6307 DOI: 10.1039/D3OB00772C

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Organic & Biomolecular Chemistry

Synthesis of (E)-2-(1-(methoxyimino)ethyl)-2-phenylbenzofuran-3(2H)-ones from (E)-1-(benzofuran-2-yl)ethan-1-one O-methyl oximes and iodobenzenes via a palladium-catalyzed dearomative arylation/oxidation reaction†

Abstract

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Synthesis of (E)-2-(1-(methoxyimino)ethyl)-2-phenylbenzofuran-3(2H)-ones from (E)-1-(benzofuran-2-yl)ethan-1-one O-methyl oximes and iodobenzenes via a palladium-catalyzed dearomative arylation/oxidation reaction

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