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Significantly Improved Method for the Pd-Catalyzed Coupling of Phenols with Aryl Halides: Understanding Ligand Effects

Carlos H. Burgos, Timothy E. Barder, Xiaohua Huang, Stephen L. Buchwald*

*Department of Chemistry, Room 18-490, Massachusetts Institute of Technology, Cambridge, MA 02139, USA, Email:

C. H. Burgos, T. E. Barder, X. Huang, S. L. Buchwald, Angew. Chem. Int. Ed., 2006, 45, 4321-4326.

DOI: 10.1002/anie.200601253

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The scope and generality of Pd-catalyzed diaryl ether formation has been improved allowing the coupling of electron-deficient aryl halides almost without any restrictions. The role of the ligand bulk in these C-O bond-forming reactions is discussed.

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Key Words

Buchwald-Hartwig coupling, diaryl ethers, biaryl phosphines, C-O bond formation, palladium, substituent effects, synthetic methods

ID: J06-Y2006-1690