Synthesis of diaryl ethers

Related

Name Reactions

Recent Literature

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

The arylation of N-H and O-H containing compounds at room temperature with phenylboronic acids is promoted in the presence of cupric acetate and a tertiary amine. Substrates include phenols, amines, anilines, amides, imides, ureas, carbamates, and sulfonamides.
D. M. T. Chan, K. L. Monaco, R.-P. Wang, M. P. Winteres, Tetrahedron Lett., 1998, 39, 2933-2936.

An efficient, mild and transition-metal-free N-arylation of amines, sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has been achieved by using various o-silylaryl triflates in the presence of CsF.
Z. Liu, R. C. Larock, J. Org. Chem., 2006, 71, 3198-3209.

1,1,1-Tris(hydroxymethyl)ethane as a New, Efficient, and Versatile Tripod Ligand for Copper-Catalyzed Cross-Coupling Reactions of Aryl Iodides with Amides, Thiols, and Phenols
Y.-J. Chen, H.-H. Chen, Org. Lett., 2006, 8, 5609-5612.

Catalyst-free direct coupling of phenols to electron-deficient aryl halides through S_NAr-based addition reactions gave diaryl ethers in very good yields within 5-10 min in refluxing DMSO with assistance of microwave irradiation.
F. Li, Q. Wang, Z. Ding, G. Tao, Org. Lett., 2003, 5, 2169-2171.

Diaryl ethers are readily synthesized in high yield at room temperature through the copper(II)-promoted coupling of arylboronic acids and phenols. The reaction is tolerant of a wide range of substituents on both coupling partners. These reaction conditions permit the racemization-free arylation of phenolic amino acids.
D. A. Evans, J. L. Katz, T. R. West, Tetrahedron Letters, 1998, 39, 2937-2940.

With either 1.0 or 0.10 equivalent of DBU, smooth desilylation of various aryl silyl ethers was accomplished selectively in the presence of base-sensitive groups such esters and alkyl silyl ethers. A direct transformation of aryl silyl ethers into biaryl ethers was possible through tandem desilylation and S_NAr reaction with activated aryl fluorides.
C.-E. Yeom, H. W. Kim, S. Y. Lee, B. M. Kim, Synlett, 2007, 146-150.