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

被引：98

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

页码：2338 / 2344

页数：7

共 50 条

[41] Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides
Weix, D. J.
Everson, D. A.
Shrestha, R.
SYNLETT, 2010, (08) : A45 - A46
[42] Nickel-Catalyzed Reductive Cross-Coupling of Heteroaryl Chlorides and Aryl Chlorides
Mirabi, Bijan
Marchese, Austin D.
Lautens, Mark
ACS CATALYSIS, 2021, 11 (20) : 12785 - 12793
[43] Electrochemical Enantioselective Nickel-Catalyzed Cross-Coupling of Aldehydes with Aryl Iodides
Hu, Liangjian
Fosso, Jospin Le Blanc Lele
Guillot, Regis
Mellah, Mohamed
Schulz, Emmanuelle
CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (71)
[44] Nickel-Catalyzed Cross-Coupling of Organolithium Reagents with (Hetero)Aryl Electrophiles
Heijnen, Dorus
Gualtierotti, Jean-Baptiste
Hornillos, Valentin
Feringa, Ben L.
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (12) : 3991 - 3995
[45] Nickel-Catalyzed Cross-Coupling of (Hetero)aryl Chlorides with Aryllithium Compounds
Tao, Jian-Long
Wang, Zhong-Xia
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (04) : 521 - 527
[46] Nickel-Catalyzed Desulfitative Suzuki-Miyaura Cross-Coupling of N,N-Disulfonylmethylamines and Arylboronic Acids
Chen, Liangshun
Lang, Hongyue
Fang, Lei
Yu, Jianjun
Wang, Limin
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (29) : 6385 - 6389
[47] Nickel-Catalyzed Photoredox-Mediated Cross-Coupling of Aryl Electrophiles and Aryl Azides
Konev, Mikhail O.
McTeague, T. Andrew
Johannes, Jeffrey W.
ACS CATALYSIS, 2018, 8 (10): : 9120 - 9124
[48] Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: synthesis of diarylsulfides
Bhowmik, Amit
Yadav, Mahesh
Fernandes, Rodney A.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (13) : 2447 - 2458
[49] Quaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents
Chen, Tie-Gen
Zhang, Haolin
Mykhailiuk, Pavel K.
Merchant, Rohan R.
Smith, Courtney A.
Qin, Tian
Baran, Phil S.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (08) : 2454 - 2458
[50] Dirhodium(II)-Catalyzed Cross-Coupling Reactions of Aryl Aldehydes with Arylboronic Acids in Water
Kuang, Yi
Wang, Yuanhua
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (06) : 1163 - 1166

← 1 2 3 4 5 →