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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Bibliographic Details
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
Format: Article
Language:English
Subjects:
Amination
Chemical synthesis
Iron
Organic chemistry
Tetrabutylammonium bromide
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Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/d1qo01687c