Palladium(II)-catalyzed ortho-arylation via phosphate-group-directed C-H activation

被引：48

作者：

Jeon, Woo Hyung ^{[1
]}

Lee, Tae Seob ^{[1
]}

Kim, Eun Jin ^{[1
]}

Moon, Bongjin ^{[1
]}

Kang, Jahyo ^{[1
]}

机构：

[1] Sogang Univ, Dept Chem, Seoul 121742, South Korea

来源：

TETRAHEDRON | 2013年 / 69卷 / 25期

关键词：

Phosphate; Palladium catalyst; C-H activation; Diaryliodonium salt; Directing group; NAPHTHALENE-CATALYZED LITHIATION; ONE-POT SYNTHESIS; ROOM-TEMPERATURE; BOND ACTIVATION; DIRECT TRANSFORMATION; DIALKYL SULFATES; PALLADIUM; ARENES; COMPLEXES; MECHANISM;

D O I：

10.1016/j.tet.2013.04.067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aryl dialkyl phosphate, which is readily available from phenol, was a good substrate for the Pd(II) catalyzed aryl aryl coupling reaction through ortho-C H activation. Although a phosphate group is regarded as a poor coordinating group, highly regioselective ortho-arylation could be achieved by employing Pd(OTf)(2)center dot 2H(2)O and Ar2IOTf as a catalyst and an aryl group source, respectively. The phosphate group of the resulting coupled product can be transformed into an aryl anion via reductive cleavage and used for further C-C bond formation. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5152 / 5159

页数：8

共 50 条

[1] Palladium-catalyzed C-H activation of anilides at room temperature: ortho-arylation and acetoxylation
Yang, Fan
Song, Feijie
Li, Wei
Lan, Jingbo
You, Jingsong
RSC ADVANCES, 2013, 3 (25): : 9649 - 9652
[2] Palladium-Catalyzed Ortho-Arylation of Benzamides via Direct sp2 C-H Bond Activation
Li, Dan-Dan
Yuan, Ting-Ting
Wang, Guan-Wu
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (07): : 3341 - 3347
[3] Palladium(II)-Catalyzed Acetoxime Directed ortho-Arylation of Aromatic Alcohols
Guo, Kun
Chen, Xiaolan
Zhang, Jingyu
Zhao, Yingsheng
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (48) : 17474 - 17478
[4] Palladium-catalyzed ortho-arylation of benzoic acid derivatives via C-H bond activation using an aminoacetic acid bidentate directing group
Zhou, Xiaomeng
Wang, Qing
Zhao, Weihua
Xu, Songsong
Zhang, Wei
Chen, Junmin
TETRAHEDRON LETTERS, 2015, 56 (06) : 851 - 855
[5] Direct ortho-arylation of 2-arylbenzoxazoles via C-H activation
Yang, Fan
Wu, Yangjie
Zhu, Zhiwu
Zhang, Junli
Li, Yanan
TETRAHEDRON, 2008, 64 (28) : 6782 - 6787
[6] Cu(II)-Promoted Palladium-Catalyzed C-H Ortho-Arylation of N,N-Dimethylbenzylamines
Feng, Ruokun
Yao, Jinzhong
Liang, Zunjun
Liu, Zhanxiang
Zhang, Yuhong
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08): : 3688 - 3696
[7] Benzylamine ortho-arylation by using C-H activation methodology
Daugulis, Olafs
Lazareva, Anna
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[8] Anilide ortho-arylation by using C-H activation methodology
Daugulis, O
Zaitsev, VG
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) : 4046 - 4048
[9] N-Tosylcarboxamide as a Transformable Directing Group for Pd-Catalyzed C-H Ortho-Arylation
Peron, Florent
Fossey, Christine
Cailly, Thomas
Fabis, Frederic
ORGANIC LETTERS, 2012, 14 (07) : 1827 - 1829
[10] Palladium(II)-Catalyzed Oxidative ortho-Arylation of 2-Phenylpyridines
Feng, Jie
Lu, Guoping
Lv, Meifang
Cai, Chun
SYNLETT, 2013, 24 (16) : 2153 - 2159

← 1 2 3 4 5 →