Palladium(II)-catalyzed Sequential ortho-olefination of β-arylethamines with assistance of oxalyl amide

被引：13

作者：

Liu, Pei ^{[1
]}

Han, Jian ^{[1
]}

Wang, Qian ^{[1
]}

Huang, Zhibin ^{[1
]}

Shi, Daqing ^{[1
]}

Zeng, Runsheng ^{[1
]}

Zhao, Ying Sheng ^{[1
]}

机构：

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

来源：

RSC ADVANCES | 2015年 / 5卷 / 74期

基金：

中国国家自然科学基金;

关键词：

C-H OLEFINATION; PALLADIUM-CATALYZED ARYLATION; BOND FUNCTIONALIZATION; DIRECTING GROUP; PD(II)-CATALYZED OLEFINATION; AROMATIC-SUBSTITUTION; C(SP(3))-H BONDS; ACTIVATION; ALKENYLATION; ARENES;

D O I：

10.1039/c5ra11677e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Pd-catalyzed highly selective ortho-alkenylation of beta-arylethamines with the assistance of oxalyl amide is developed. A wide range of olefins such as allyl acetate, allyl alcohol derivatives, terminal alkenes, acraldehyde, acrylate, acrylonitrile, neohexene and styrene derivatives are all tolerable, which is the broadest yet reported for this kind of C-H transformation. Furthermore, sequential functionalization of beta-arylethamine is also achieved well in one pot.

引用

页码：60646 / 60649

页数：4

共 60 条

[1] Ruthenium-catalyzed aerobic oxidative coupling of alkynes with 2-aryl-substituted pyrroles [J].

Ackermann, Lutz ;

Wang, Lianhui ;

Lygin, Alexander V. .

CHEMICAL SCIENCE, 2012, 3 (01) :177-180

[2] Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds [J].

Ackermann, Lutz ;

Lygin, Alexander V. ;

Hofmann, Nora .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) :6379-6382

[3] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[4]

[Anonymous], 2011, ANGEW CHEM, V123, P10054

[5]

[Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANIE.201201666

[6]

[Anonymous], 2011, ANGEW CHEM-GER EDIT

[7]

[Anonymous], 2013, Angew. Chem, DOI DOI 10.1002/ANGE.201301451

[8]

Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]

[9] Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: Regioselective and switchable C-H alkenylation and annulation of pyrroles [J].

Beck, EM ;

Grimster, NP ;

Hatley, R ;

Gaunt, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2528-2529

[10] Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].

Boele, MDK ;

van Strijdonck, GPF ;

de Vries, AHM ;

Kamer, PCJ ;

de Vries, JG ;

van Leeuwen, PWNM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587

← 1 2 3 4 5 6 →