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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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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container_title Organic chemistry frontiers an international journal of organic chemistry
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creator Bashir, Muhammad Adnan
Tang, Langyu
Li, Longjie
Yu, Huaibin
Yao, Weijun
Wu, Guojiao
Zhong, Fangrui
description 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.
doi_str_mv 10.1039/d1qo01942b
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subjects Bonding
Carbonyl compounds
Carbonyls
Covalent bonds
Dehydrogenation
Diaryl ethers
Ethers
Organic chemistry
Phenols
Quinones
title Formal dual C(sp2)–H cross-dehydrogenative C–O bond formation to construct highly functionalized diaryl ethers with O2
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