Synthesis of highly functionalized diaryl ethers by copper-mediated O-arylation of phenols using trivalent arylbismuth reagents

Chemistry : a European Journal
Cynthia CrifarAlexandre Gagnon

Abstract

Highly functionalized diaryl ethers were prepared by copper(II) acetate mediated O-arylation reaction of phenols using trivalent organobismuthanes. The reaction is performed under simple conditions and tolerates a wide diversity of functional groups on the phenol and on the organobismuth reagent. Substoichiometric amounts of catalyst can be used by performing the reaction under an oxygen atmosphere. The N-arylation of pyridones is also reported.

References

Jan 4, 2007·Journal of the American Chemical Society·Alexandre GagnonFrancis Barabé
Mar 28, 2008·The Journal of Organic Chemistry·Alexandre GagnonFrancis Barabé
Aug 15, 2009·Angewandte Chemie·Florian Monnier, Marc Taillefer
Nov 11, 2009·Journal of the American Chemical Society·Debabrata Maiti, Stephen L Buchwald
Feb 10, 2010·The Journal of Organic Chemistry·Debabrata Maiti, Stephen L Buchwald
Feb 16, 2011·Organic Letters·Nazli JalalianBerit Olofsson
Sep 28, 2012·Chemistry : a European Journal·Nazli JalalianBerit Olofsson

Citations

Aug 4, 2016·The Journal of Organic Chemistry·Seo-Hee JungWon-Suk Kim
Dec 17, 2014·Organic & Biomolecular Chemistry·Pauline PetiotAlexandre Gagnon
Jul 12, 2019·Beilstein Journal of Organic Chemistry·Emeline BenoitAlexandre Gagnon
Aug 9, 2019·Acta Crystallographica. Section E, Crystallographic Communications·Mauro BarberoValentina Colombo
Feb 29, 2020·Nature Chemistry·Mark JurratLiam T Ball

Related Concepts

Bismuth
Catalysis
Copper
Ethers
Phenols
Oxygen
Pyridones
Cupric acetate
Phenolics
Trivalent influenza vaccine

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