Palladium-Catalyzed Oxalyl Amide Directed Silylation and Germanylation of Amine Derivatives

被引：77

作者：

Chen, Changpeng ^{[1
]}

Guan, Mingyu ^{[1
]}

Zhang, Jingyu ^{[2
,3
]}

Wen, Zhenkang ^{[4
]}

Zhao, Yingsheng ^{[1
]}

机构：

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

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

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

[4] Shanxi Univ, Coll Chem & Chem Engn, Taiyuan 030006, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 15期

基金：

中国国家自然科学基金;

关键词：

C-H SILYLATION; CARBON-HYDROGEN BONDS; C(SP(3))-H BONDS; ARENES; HYDROSILANES; C(SP(2))-H; ARYL; ACTIVATION; ASSISTANCE; ARYLATION;

D O I：

10.1021/acs.orglett.5b01393

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed direct ortho-silylation of oxalyl amide-protected phenylmethanamine and phenethylamine with commercially available disilanes is reported. Germanylation products were also produced under the same reaction conditions. This protocol tolerated oxalyl amide-protected aliphatic, amines, which gave gamma-C-H silylation products.

引用

页码：3646 / 3649

页数：4

共 36 条

[1] Trimethylsilylpyrazoles as novel inhibitors of p38 MAP kinase: A new use of silicon bioisosteres in medicinal chemistry [J].

Barnes, Matthew J. ;

Conroy, Richard ;

Miller, David J. ;

Mills, John S. ;

Montana, John G. ;

Pooni, Parminder K. ;

Showell, Graham A. ;

Walsh, Louise M. ;

Warneck, Julie B. H. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (02) :354-357

[2] Palladium-Catalyzed ortho-Selective C-H Fluorination of Oxalyl Amide-Protected Benzylamines [J].

Chen, Changpeng ;

Wang, Chao ;

Zhang, Jingyu ;

Zhao, Yingsheng .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02) :942-949

[3] Catalytic Silylation of Unactivated C-H Bonds [J].

Cheng, Chen ;

Hartwig, John F. .

CHEMICAL REVIEWS, 2015, 115 (17) :8946-8975

[4] Iridium-Catalyzed Silylation of Aryl C-H Bonds [J].

Cheng, Chen ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (02) :592-595

[5] Rhodium-Catalyzed Intermolecular C-H Silylation of Arenes with High Steric Regiocontrol [J].

Cheng, Chen ;

Hartwig, John F. .

SCIENCE, 2014, 343 (6173) :853-857

[6] Reactions of hydrosilanes with transition-metal complexes: Formation of stable transition-metal silyl compounds [J].

Corey, JY ;

Braddock-Wilking, J .

CHEMICAL REVIEWS, 1999, 99 (01) :175-292

[7] Pd-Catalyzed Oxidative ortho-C-H Borylation of Arenes [J].

Dai, Hui-Xiong ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) :134-137

[8] Organosilicon Molecules with Medicinal Applications [J].

Franz, Annaliese K. ;

Wilson, Sean O. .

JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (02) :388-405

[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] Direct synthesis of aryl halosilanes through iridium(I)-catalyzed aromatic C-H silylation by disilanes [J].

Ishiyama, T ;

Sato, K ;

Nishio, Y ;

Miyaura, N .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (43) :5346-5348

← 1 2 3 4 →