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

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 goo...

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Published in:Organic chemistry frontiers an international journal of organic chemistry 2022-01, Vol.9 (2), p.380-385
Main Authors: Yan-Hui, Fan, Xiao-Yu, Guan, Wen-Pei, Li, Cheng-Zhou, Lin, De-Xian, Bing, Mei-Zhi Sun, Guo, Cheng, Cao, Jing, Jun-Jie, Chen, Qing-Hai Deng
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Language:English
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Amination
Chemical synthesis
Iron
Organic chemistry
Tetrabutylammonium bromide
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container_title Organic chemistry frontiers an international journal of organic chemistry
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creator Yan-Hui, Fan
Xiao-Yu, Guan
Wen-Pei, Li
Cheng-Zhou, Lin
De-Xian, Bing
Mei-Zhi Sun
Guo, Cheng
Cao, Jing
Jun-Jie, Chen
Qing-Hai Deng
description 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.
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subjects Amination
Chemical synthesis
Iron
Organic chemistry
Tetrabutylammonium bromide
title Synthesis of amidines via iron-catalyzed dearomative amination of β-naphthols with oxadiazolones
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