A General Direct Arylation of Polyfluoroarenes with Heteroaryl and Aryl Chlorides Catalyzed by Palladium Indolylphosphine Complexes

被引：21

作者：

Yuen, On Ying ^{[1
,2
]}

Charoensak, Mueangkaew ^{[3
,4
]}

So, Chau Ming ^{[1
,2
]}

Kuhakarn, Chutima ^{[3
,4
]}

Kwong, Fuk Yee ^{[1
,2
]}

机构：

[1] Hong Kong Polytech Univ, State Key Lab Chirosci, Kowloon, Hong Kong, Peoples R China

[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China

[3] Mahidol Univ, Fac Sci, Dept Chem, Bangkok 10400, Thailand

[4] Mahidol Univ, Fac Sci, Ctr Excellence Innovat Chem PERCH CIC, Bangkok 10400, Thailand

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2015年 / 10卷 / 04期

关键词：

aryl chlorides; CH arylation; palladium; phosphine; polyfluoroarenes; CROSS-COUPLING REACTIONS; ELECTRON-DEFICIENT POLYFLUOROARENES; PHOSPHINE-LIGANDS; MESYLATES; HALIDES; HETEROCYCLES; PRECATALYST; SELECTIVITY; ACTIVATION; DISCOVERY;

D O I：

10.1002/asia.201500048

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first general examples of direct coupling of heteroaryl chlorides, especially substituted 2-pyridyl chlorides which were previously found to be problematic, with electron-deficient polyfluoroarenes are reported. Pd(OAc)(2) associated with 3-(dicyclohexylphosphino)-2-phenylindole L1 serves as the effective catalyst which allows the challenging direct coupling of heteroaryl chlorides and polyfluoroarenes. In addition to heterocycles, a wide range of non-activated and activated aryl chlorides and alkenyl chlorides were also applicable under this catalyst system. A catalyst loading down to 1mol% Pd can be achieved.

引用

页码：857 / 861

页数：5

共 50 条

[1] Palladium-catalyzed direct arylation of polyfluoroarenes with aryl tosylates and mesylates
Lee, Dong Sheng
Choy, Pui Ying
So, Chau Ming
Wang, Jun
Lau, Chak Po
Kwong, Fuk Yee
[J]. RSC ADVANCES, 2012, 2 (24): : 9179 - 9182
[2] Palladium-Catalyzed Direct Intermolecular α-Arylation of Amides with Aryl Chlorides
Zheng, Bing
Jia, Tiezheng
Walsh, Patrick J.
[J]. ORGANIC LETTERS, 2013, 15 (16) : 4190 - 4193
[3] New ligands for a general palladium-catalyzed amination of aryl and heteroaryl chlorides
Rataboul, F
Zapf, A
Jackstell, R
Harkal, S
Riermeier, T
Monsees, A
Dingerdissen, U
Beller, M
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (12) : 2983 - 2990
[4] Mild and general methods for the palladium-catalyzed cyanation of aryl and heteroaryl chlorides
Littke, Adam
Soumeillant, Maxime
Kaltenbach, Robert F., III
Cherney, Robert J.
Tarby, Christine M.
Kiau, Susanne
[J]. ORGANIC LETTERS, 2007, 9 (09) : 1711 - 1714
[5] Palladium-Catalyzed Direct Arylation of Polyfluoroarenes with Organosilicon Reagents
Fan, Huixin
Shang, Yaping
Su, Weiping
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (16) : 3323 - 3327
[6] Palladium-Catalyzed α-Arylation of Sultams with Aryl and Heteroaryl Iodides
Rene, Olivier
Fauber, Benjamin P.
Malhotra, Sushant
Yajima, Herbert
[J]. ORGANIC LETTERS, 2014, 16 (13) : 3468 - 3471
[7] Ligand-free Palladium/Copper Co-catalyzed Direct Arylation of Polyfluoroarenes with Aryl Iodides
Zhang, Xinyan
Yu, Jian
Yan, Guobing
[J]. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2013, 68 (08): : 885 - 890
[8] DIRECT β-ARYLATION OF FURANS WITH ARYL IODIDES CATALYZED BY DINUCLEAR PALLADIUM COMPLEXES
Goto, Takahiro
Kato, Hayate
Tsukada, Naofumi
[J]. HETEROCYCLES, 2017, 94 (12) : 2222 - 2228
[9] A General Palladium-Catalyzed Hiyama Cross-Coupling Reaction of Aryl and Heteroaryl Chlorides
Yuen, On Ying
So, Chau Ming
Man, Ho Wing
Kwong, Fuk Yee
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (19) : 6471 - 6476
[10] Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides
Zheng, Bing
Li, Minyan
Gao, Gui
He, Yuying
Walsh, Patrick J.
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (13) : 2156 - 2162

← 1 2 3 4 5 →