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

被引：74

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
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.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (02) : 354 - 357
[2] Palladium-Catalyzed ortho-Selective C-H Fluorination of Oxalyl Amide-Protected Benzylamines
Chen, Changpeng
Wang, Chao
Zhang, Jingyu
Zhao, Yingsheng
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02) : 942 - 949
[3] Catalytic Silylation of Unactivated C-H Bonds
Cheng, Chen
Hartwig, John F.
[J]. CHEMICAL REVIEWS, 2015, 115 (17) : 8946 - 8975
[4] Iridium-Catalyzed Silylation of Aryl C-H Bonds
Cheng, Chen
Hartwig, John F.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (02) : 592 - 595
[5] Rhodium-Catalyzed Intermolecular C-H Silylation of Arenes with High Steric Regiocontrol
Cheng, Chen
Hartwig, John F.
[J]. SCIENCE, 2014, 343 (6173) : 853 - 857
[6] Reactions of hydrosilanes with transition-metal complexes: Formation of stable transition-metal silyl compounds
Corey, JY
Braddock-Wilking, J
[J]. CHEMICAL REVIEWS, 1999, 99 (01) : 175 - 292
[7] Pd-Catalyzed Oxidative ortho-C-H Borylation of Arenes
Dai, Hui-Xiong
Yu, Jin-Quan
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) : 134 - 137
[8] Organosilicon Molecules with Medicinal Applications
Franz, Annaliese K.
Wilson, Sean O.
[J]. 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
Han, Jian
Liu, Pei
Wang, Chao
Wang, Qian
Zhang, Jingyu
Zhao, Yanwei
Shi, Daqing
Huang, Zhibin
Zhao, Yingsheng
[J]. ORGANIC LETTERS, 2014, 16 (21) : 5682 - 5685
[10] Direct synthesis of aryl halosilanes through iridium(I)-catalyzed aromatic C-H silylation by disilanes
Ishiyama, T
Sato, K
Nishio, Y
Miyaura, N
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (43) : 5346 - 5348

← 1 2 3 4 →