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A Catalyst‐Controlled Aerobic Coupling of ortho ‐Quinones and Phenols Applied to the Synthesis of Aryl Ethers
Author(s) -
Huang Zheng,
Lumb JeanPhilip
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201606359
Subject(s) - phenols , catalysis , aryl , chemistry , reactivity (psychology) , substrate (aquarium) , quinone , yield (engineering) , transition metal , copper , organic chemistry , combinatorial chemistry , covalent bond , materials science , medicine , alkyl , alternative medicine , oceanography , pathology , metallurgy , geology
Abstract ortho ‐Quinones are underutilized six‐carbon‐atom building blocks. We herein describe an approach for controlling their reactivity with copper that gives rise to a catalytic aerobic cross‐coupling with phenols. The resulting aryl ethers are generated in high yield across a broad substrate scope under mild conditions. This method represents a unique example where the covalent modification of an ortho ‐quinone is catalyzed by a transition metal, creating new opportunities for their utilization in synthesis.