Nickel-Catalyzed Cross-Coupling of Aryl Phosphates with Arylboronic Acids

被引：99

作者：

Chen, Hu ^{[1
,2
]}

Huang, Zhongbin ^{[1
,2
]}

Hu, Xiaoming ^{[1
,2
]}

Tang, Guo ^{[1
,2
,4
]}

Xu, Pengxiang ^{[1
,2
]}

Zhao, Yufen ^{[1
,2
,3
]}

Cheng, Chien-Hong ^{[4
]}

机构：

[1] Xiamen Univ, Coll Chem & Chem Engn, Dept Chem, Xiamen 361005, Fujian, Peoples R China

[2] Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Fujian, Peoples R China

[3] Tsinghua Univ, Minist Educ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China

[4] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 07期

关键词：

TEMPERATURE SUZUKI-MIYAURA; CARBON-CARBON BONDS; C-O ACTIVATION; BORONIC ACIDS; ALKENYL PHOSPHATES; ORGANOBORON COMPOUNDS; GRIGNARD-REAGENTS; ENOL ETHERS; ESTERS; ALKYNES;

D O I：

10.1021/jo2000034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Suzuki-Miyaura cross-coupling of aryl phosphates using Ni(PCy(3))(2)Cl(2) as an inexpensive, bench-stable catalyst is described. Broad substrate scope and high efficiency are demonstrated by the syntheses of more than 40 biaryls and by constructing complex organic molecules. The poor reactivity of aryl phosphates relative to aryl halides is successfully employed to construct polyarenes by selective cross-coupling using Pd and Ni catalysts.

引用

收藏

页码：2338 / 2344

页数：7

相关论文

共 51 条

[1] RATES AND MECHANISM OF BIPHENYL SYNTHESIS CATALYZED BY ELECTROGENERATED COORDINATIVELY UNSATURATED NICKEL-COMPLEXES [J].

AMATORE, C ;

JUTAND, A .

ORGANOMETALLICS, 1988, 7 (10) :2203-2214

[2]

[Anonymous], 2004, METAL CATALYZED CROS

[3] N,N-Diethyl O-Carbamate: Directed Metalation Group and Orthogonal Suzuki-Miyaura Cross-Coupling Partner [J].

Antoft-Finch, Aurora ;

Blackburn, Tom ;

Snieckus, Victor .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (49) :17750-17752

[4] Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters [J].

Billingsley, Kelvin ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) :3358-3366

[5] A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds [J].

Billingsley, Kelvin L. ;

Anderson, Kevin W. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (21) :3484-3488

[6] Copper-Catalyzed Aerobic Oxidative Coupling of Terminal Alkynes with H-Phosphonates Leading to Alkynylphosphonates [J].

Gao, Yuxing ;

Wang, Gang ;

Chen, Lu ;

Xu, Pengxiang ;

Zhao, Yufen ;

Zhou, Yongbo ;

Han, Li-Biao .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (23) :7956-+

[7] A Ligand Free and Room Temperature Protocol for Pd-Catalyzed Kumada-Corriu Couplings of Unactivated Alkenyl Phosphates [J].

Gauthier, Delphine ;

Beckendorf, Stephan ;

Gogsig, Thomas M. ;

Lindhardt, Anders T. ;

Skrydstrup, Troels .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09) :3536-3539

[8] C(aryl)-O Activation of Aryl Carboxylates in Nickel-Catalyzed Biaryl Syntheses [J].

Goossen, Lukas J. ;

Goossen, Kaethe ;

Stanciu, Corneliu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (20) :3569-3571

[9] Biaryl Construction via Ni-Catalyzed C-O Activation of Phenolic Carboxylates [J].

Guan, Bing-Tao ;

Wang, Yang ;

Li, Bi-Jie ;

Yu, Da-Gang ;

Shi, Zhang-Jie .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) :14468-+

[10] Direct benzylic alkylation via Ni-catalyzed selective benzylic sp3 C-O activation [J].

Guan, Bing-Tao ;

Xiang, Shi-Kai ;

Wang, Bi-Qin ;

Sun, Zuo-Peng ;

Wang, Yang ;

Zhao, Ke-Qing ;

Shi, Zhang-Jie .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3268-+

← 1 2 3 4 5 6 →