A general and mild Ullmann-type synthesis of diaryl ethers

被引：286

作者：

Cristau, HJ ^{[1
]}

Cellier, PP ^{[1
]}

Hamada, S ^{[1
]}

Spindler, JF ^{[1
]}

Taillefer, M ^{[1
]}

机构：

[1] Ecole Natl Super Chim Montpellier, Chim Organ Lab, CNRS, UMR 5076, F-34296 Montpellier 5, France

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 06期

关键词：

D O I：

10.1021/ol036290g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the synthesis of diaryl ethers under particularly mild conditions is described. Inexpensive ligands were found to greatly accelerate the Ullmann-type coupling of aryl bromides or iodides with phenols. A series of diaryl ethers were obtained with excellent yields in acetonitrile in the presence Of Cs2CO3 and catalytic copper(l) oxide. The reaction tolerates substrates with unfavorable substitution patterns, such as sterically hindered coupling partners or electron-rich aryl halides.

引用

页码：913 / 916

页数：4

共 39 条

[1]

[Anonymous], [No title captured]

[2] Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers [J].

Aranyos, A ;

Old, DW ;

Kiyomori, A ;

Wolfe, JP ;

Sadighi, JP ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4369-4378

[3] COPPER-SALTS CATALYSIS OF N-PHENYLATION OF AMINES BY TRIVALENT ORGANOBISMUTH COMPOUNDS [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J .

TETRAHEDRON LETTERS, 1987, 28 (08) :887-890

[4] COPPER CATALYZED O-PHENYLATION OF PHENOLS AND ENOLS BY PENTAVALENT ORGANOBISMUTH COMPOUNDS [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J ;

PICHON, C .

TETRAHEDRON LETTERS, 1986, 27 (31) :3619-3622

[5] Selective N(1)-arylation of benzotriazole with activated aryl halides under conditions of phase transfer catalysis [J].

Beletskaya, IP ;

Davydov, DV ;

Gorovoi, MS ;

Kardashov, SV .

RUSSIAN CHEMICAL BULLETIN, 1999, 48 (08) :1533-1536

[6] TOTAL SYNTHESIS OF BOUVARDIN, O-METHYLBOUVARDIN, AND O-METHYL-N-9-DESMETHYLBOUVARDIN [J].

BOGER, DL ;

PATANE, MA ;

ZHOU, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8544-8556

[7] Ullmann diaryl ether synthesis: Rate acceleration by 2,2,6,6-tetramethylheptane-3,5-dione [J].

Buck, E ;

Song, ZJ ;

Tschaen, D ;

Dormer, PG ;

Volante, RP ;

Reider, PJ .

ORGANIC LETTERS, 2002, 4 (09) :1623-1626

[8] Copper promoted C-N and C-O bond cross-coupling with phenyl and pyridylboronates [J].

Chan, DMT ;

Monaco, KL ;

Li, RH ;

Bonne, D ;

Clark, CG ;

Lam, PYS .

TETRAHEDRON LETTERS, 2003, 44 (19) :3863-3865

[9] Mild conditions for copper-catalysed N-arylation of pyrazoles [J].

Cristau, HJ ;

Cellier, PP ;

Spindler, JF ;

Taillefer, M .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (04) :695-709

[10] AN ASSESSMENT OF THE CAUSES OF THE CESIUM EFFECT [J].

DIJKSTRA, G ;

KRUIZINGA, WH ;

KELLOGG, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4230-4234

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