An efficient catalyst system for diaryl ether synthesis from aryl chlorides

被引：119

作者：

Harkal, S

Kumar, K

Michalik, D

Zapf, A

Jackstell, R

Rataboul, F

Riermeier, T

Monsees, A

Beller, M

机构：

[1] Univ Rostock EV, Leibniz Inst Organ Katalyse, IFOK, D-18055 Rostock, Germany

[2] Degussa AG, D-63457 Hanau, Germany

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 18期

关键词：

aryl chlorides; aryl ethers; etherification palladium; phosphines;

D O I：

10.1016/j.tetlet.2005.03.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The combination of 2-phosphino-substituted N-arylpyrroles or related indoles (cataCXium (R) P) and Pd(OAc)(2) allows for efficient cross-coupling reactions of aryl chlorides and phenols to give diaryl ethers. A variety of aryl and heteroaryl chlorides can be coupled with substituted phenols showing unprecedented catalyst turnover numbers. (c) 2005 Published by Elsevier Ltd.

引用

页码：3237 / 3240

页数：4

共 41 条

[11] VANCOMYCIN - STRUCTURE AND TRANSFORMATION TO CDP-I
HARRIS, CM
KOPECKA, H
HARRIS, TM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (23) : 6915 - 6922
[12] Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C-C, C-N, and C-O bond-forming cross-couplings
Kataoka, N
Shelby, Q
Stambuli, JP
Hartwig, JF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) : 5553 - 5566
[13] Palladium-catalyzed intramolecular C-O bond formation
Kuwabe, S
Torraca, KE
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (49) : 12202 - 12206
[14] COPPER ASSISTED NUCLEOPHILIC-SUBSTITUTION OF ARYL HALOGEN
LINDLEY, J
[J]. TETRAHEDRON, 1984, 40 (09) : 1433 - 1456
[15] Littke AF, 2002, ANGEW CHEM INT EDIT, V41, P4176, DOI 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO
[16] 2-U
[17] Palladium alkoxides: Potential intermediacy in catalytic amination, reductive elimination of ethers, and catalytic etheration. Comments on alcohol elimination from Ir(III)
Mann, G
Hartwig, JF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (51) : 13109 - 13110
[18] Palladium-catalyzed C-O coupling involving unactivated aryl halides. Sterically induced reductive elimination to form the C-O bond in diaryl ethers
Mann, G
Incarvito, C
Rheingold, AL
Hartwig, JF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) : 3224 - 3225
[19] Palladium-catalyzed formation of diaryl ethers from aryl bromides. Electron poor phosphines enhance reaction yields
Mann, G
Hartwig, JF
[J]. TETRAHEDRON LETTERS, 1997, 38 (46) : 8005 - 8008
[20] A general copper-catalyzed synthesis of diaryl ethers
Marcoux, JF
Doye, S
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (43) : 10539 - 10540

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