Pd-Catalyzed thiophene directed regioselective functionalization of arenes: a direct approach to multiply-substituted benzyl amines

被引：7

作者：

Hu, Jundie ^{[1
]}

Li, Guobao ^{[1
]}

Huang, Zhi-Bin ^{[1
]}

Zhang, Jingyu ^{[2
,3
]}

Shi, Da-Qing ^{[1
]}

Zhao, Yingsheng ^{[1
]}

机构：

[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China

[2] Soochow Univ, Coll Phys Optoelect & Energy, Suzhou 215006, Peoples R China

[3] Soochow Univ, Collaborat Innovat Ctr Suzhou Nano Sci & Technol, Suzhou 215006, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2017年 / 4卷 / 08期

基金：

中国国家自然科学基金;

关键词：

C-H HETEROARYLATION; ORTHO-OLEFINATION; ORTHO-ARYLATION; ALKENYLATION; ACTIVATION; MECHANISM; ACCESS; BOND; DERIVATIVES; ACIDS;

D O I：

10.1039/c7qo00236j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of employing thiophene as the coordination center to assist C-H functionalization via a palladium catalyst has been described. The synthetically challenging penta-substituted benzylamines with five different functional groups could be easily achieved by taking advantage of transitive oxalyl amide/thiophene-directed C-H functionalization, which highlights its versatility in the construction of multiply-substituted arenes. The penta-substituted benzylamine displays its potential nature as a hole-transporting material.

引用

页码：1503 / 1507

页数：5

共 42 条

[1] Direct ortho-Arylation of ortho-Substituted Benzoic Acids: Overriding Pd-Catalyzed Protodecarboxylation [J].

Arroniz, Carlos ;

Ironmonger, Alan ;

Rassias, Gerry ;

Larrosa, Igor .

ORGANIC LETTERS, 2013, 15 (04) :910-913

[2]

Askew B. C., 2009, Patent No. [WO2009- US291, 291]

[3] Palladium-Catalyzed Ortho-Arylation of Carbamate-Protected Estrogens [J].

Bedford, Robin B. ;

Brenner, Peter B. ;

Durrant, Steven J. ;

Gallagher, Timothy ;

Mendez-Galvez, Carolina ;

Montgomery, Michelle .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (09) :3473-3478

[4] Synthesis and biological evaluation of benzimidazole derivatives as potent AMP-activated protein kinase activators [J].

Charton, Julie ;

Girault-Mizzi, Sophie ;

Debreu-Fontaine, Marie-Ange ;

Foufelle, Fablenne ;

Hainault, Isabelle ;

Bizot-Espiard, Jean-Guy ;

Caignard, Daniel-Henri ;

Sergheraert, Christian .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (13) :4490-4518

[5]

Dijcks F. A., 1999, PCT Int. Appl, Patent No. [WO1998- EP6651, 6651]

[6] Ligand-Enabled meta-Selective C-H Arylation of Nosyl-Protected Phenethylamines, Benzylamines, and 2-Aryl Anilines [J].

Ding, Qiuping ;

Ye, Shengqing ;

Cheng, Guolin ;

Wang, Peng ;

Farmer, Marcus E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (01) :417-425

[7] Rhodium or Ruthenium-Catalyzed Oxidative C?H/C?H Cross-Coupling: Direct Access to Extended p-Conjugated Systems [J].

Dong, Jiaxing ;

Long, Zhen ;

Song, Feijie ;

Wu, Ningjie ;

Guo, Qiang ;

Lan, Jingbo ;

You, Jingsong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (02) :580-584

[8] Ligand-Accelerated C-H Activation Reactions: Evidence for a Switch of Mechanism [J].

Engle, Keary M. ;

Wang, Dong-Hui ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (40) :14137-14151

[9] Oxalyl Amide Assisted Palladium-Catalyzed Arylation of C(sp2)-H Bond at the δ Position [J].

Han, Jian ;

Liu, Pei ;

Wang, Chao ;

Wang, Qian ;

Zhang, Jingyu ;

Zhao, Yanwei ;

Shi, Daqing ;

Huang, Zhibin ;

Zhao, Yingsheng .

ORGANIC LETTERS, 2014, 16 (21) :5682-5685

[10] Rhodium(III)-Catalyzed ortho-Arylation of Anilides with Aryl Halides [J].

Haridharan, Radhakrishnan ;

Muralirajan, Krishnamoorthy ;

Cheng, Chien-Hong .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (2-3) :366-370

← 1 2 3 4 5 →