Pd/C as a reusable catalyst for the coupling reaction of halophenols and arylboronic acids in aqueous media

被引：261

作者：

Sakurai, H

Tsukuda, T

Hirao, T

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

[2] Inst Mol Sci, Okazaki, Aichi 4448585, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 08期

关键词：

D O I：

10.1021/jo016342k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pd/C was found to catalyze the Suzuki-Miyaura coupling reaction of halophenols in aqueous media. When halophenols were treated with ArB(OH)(2) and a catalytic amount of 10% Pd/C (0.3 mol % Pd) in aqueous K2CO3 solution, the corresponding hydroxybiaryls were obtained in a high yield or quantitatively. The palladium catalyst was easily recovered and reused.

引用

页码：2721 / 2722

页数：2

共 17 条

[1] ARYLOXENIUM IONS - GENERATION FROM N-(ARYLOXY)PYRIDINIUM TETRAFLUOROBORATES AND REACTION WITH ANISOLE AND BENZONITRILE
ABRAMOVITCH, RA
ALVERNHE, G
BARTNIK, R
DASSANAYAKE, NL
INBASEKARAN, MN
KATO, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (15) : 4558 - 4565
[2] Highly efficient palladium-catalyzed boronic acid coupling reactions in water: Scope and limitations
Badone, D
Baroni, M
Cardamone, R
Ielmini, A
Guzzi, U
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) : 7170 - 7173
[3] SYNTHESIS OF DIARYLS FROM PHENYLBORIC ACID AND ARYL IODIDES IN AN AQUEOUS-MEDIUM
BUMAGIN, NA
BYKOV, VV
BELETSKAYA, IP
[J]. BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1989, 38 (10): : 2206 - 2206
[4] STRUCTURAL AND SOLVENT ELECTROLYTE EFFECTS ON THE SELECTIVITY AND EFFICIENCY OF THE ANODIC-OXIDATION OF PARA-SUBSTITUTED AROMATIC ETHERS - AN EFFICIENT ROUTE TO QUINOL ETHER KETALS AND QUINOL ETHERS
CAPPARELLI, MP
DESCHEPPER, RE
SWENTON, JS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) : 4953 - 4961
[5] Multikilogram-scale synthesis at a biphenyl carboxylic acid derivative using a Pd/C-mediated Suzuki coupling approach
Ennis, DS
McManus, J
Wood-Kaczmar, W
Richardson, J
Smith, GE
Carstairs, A
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1999, 3 (04) : 248 - 252
[6] One-step synthesis of biphenylacetic acids via Pd/C-catalyzed arylation
Gala, D
Stamford, A
Jenkins, J
Kugelman, M
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1997, 1 (02) : 163 - 164
[7] Mechanisms of the photochemical rearrangement of diphenyl ethers
Haga, N
Takayanagi, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) : 735 - 745
[8] Discovery of potent nonpeptide inhibitors of stromelysin using SAR by NMR
Hajduk, PJ
Sheppard, G
Nettesheim, DG
Olejniczak, ET
Shuker, SB
Meadows, RP
Steinman, DH
Carrera, GM
Marcotte, PA
Severin, J
Walter, K
Smith, H
Gubbins, E
Simmer, R
Holzman, TF
Morgan, DW
Davidsen, SK
Summers, JB
Fesik, SW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (25) : 5818 - 5827
[9] Suzuki coupling with ligandless palladium and potassium fluoride
Kabalka, GW
Namboodiri, V
Wang, L
[J]. CHEMICAL COMMUNICATIONS, 2001, (08) : 775 - 775
[10] Activation of aryl chlorides for Suzuki cross-coupling by ligandless, heterogeneous palladium
LeBlond, CR
Andrews, AT
Sun, YK
Sowa, JR
[J]. ORGANIC LETTERS, 2001, 3 (10) : 1555 - 1557

← 1 2 →