Formal dual C(sp2)–H cross-dehydrogenative C–O bond formation to construct highly functionalized diaryl ethers with O2

A formal dual C(sp2)–H cross-dehydrogenative C–O bond formation between phenols and N-substituted naphthylamines to expediently assemble diversely functionalized diaryl ethers bearing hydroxyl and amino functionalities with excellent atom and step economy was developed under mild conditions. The rea...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2022-04, Vol.9 (8), p.2249-2255
Main Authors: Bashir, Muhammad Adnan, Tang, Langyu, Li, Longjie, Yu, Huaibin, Yao, Weijun, Wu, Guojiao, Zhong, Fangrui
Format: Article
Language:English
Subjects:
Bonding
Carbonyl compounds
Carbonyls
Covalent bonds
Dehydrogenation
Diaryl ethers
Ethers
Organic chemistry
Phenols
Quinones
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Summary:A formal dual C(sp2)–H cross-dehydrogenative C–O bond formation between phenols and N-substituted naphthylamines to expediently assemble diversely functionalized diaryl ethers bearing hydroxyl and amino functionalities with excellent atom and step economy was developed under mild conditions. The reaction features three C–H cleavages and three C–O bond formations in one pot. In addition a rare C(sp2)–O bond formation rather than the conventional C–C bond formation took place by addition to a carbonyl O atom of the in situ generated ortho-quinone.
ISSN:2052-4110
2052-4110
DOI:10.1039/d1qo01942b