Synthesis of amidines via iron-catalyzed dearomative amination of β-naphthols with oxadiazolones

Yan-Hui Fan; Xiao-Yu Guan; Wen-Pei Li; Cheng-Zhou Lin; De-Xian Bing; Mei-Zhi Sun; Guo Cheng; Jing Cao; Jun-Jie Chen; Qing-Hai Deng

doi:10.1039/D1QO01687C

Synthesis of amidines via iron-catalyzed dearomative amination of β-naphthols with oxadiazolones†

Yan-Hui Fan,‡^a Xiao-Yu Guan,‡^a Wen-Pei Li,^a Cheng-Zhou Lin,^a De-Xian Bing,^a Mei-Zhi Sun,^a Guo Cheng,^a Jing Cao,*^a Jun-Jie Chen^a and Qing-Hai Deng

*^a

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* Corresponding authors

^a The Education Ministry Key Lab of Resource Chemistry, Joint International Research Laboratory of Resource Chemistry, Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, and Shanghai Frontiers Science Center of Biomimetic Catalysis, College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200234, China
E-mail: caojing@shnu.edu.cn, qinghaideng@shnu.edu.cn

Abstract

An iron-catalyzed dearomative amination of β-naphthols via a nitrene-transfer process has been developed. Oxadiazolones, which have rarely been applied for the synthesis of amidines, are used as the nitrene source. A variety of amidines bearing β-naphthalenone moieties were generated smoothly in good to high yields (up to 98%) in the presence of 1.5 equivalents of tetrabutylammonium bromide, which was added as an essential additive.

This article is part of the themed collection: 2021 Organic Chemistry Frontiers HOT articles

Organic Chemistry Frontiers

Synthesis of amidines via iron-catalyzed dearomative amination of β-naphthols with oxadiazolones†

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Synthesis of amidines via iron-catalyzed dearomative amination of β-naphthols with oxadiazolones

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