Palladium-Catalyzed ortho-Selective C-H Fluorination of Oxalyl Amide-Protected Benzylamines

被引：41

作者：

Chen, Changpeng ^{[1
]}

Wang, Chao ^{[1
]}

Zhang, Jingyu ^{[2
,3
]}

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, 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：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 02期

基金：

中国国家自然科学基金;

关键词：

COPPER-MEDIATED FLUORINATION; REDUCTIVE ELIMINATION; BOND FORMATION; ARYL; C(SP(2))-H; CONVERSION; AUXILIARY; MECHANISM; DELTA;

D O I：

10.1021/jo502365b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and efficient synthetic method for o-fluorobenzylamines via palladium catalyst using an easily accessible oxalyl amide as directing group has been developed. The cheap N-fluorobenzenesulfonimide could be used as an effective [F+] source and t-amyl-OH as the solvent with Pd(OAc)(2) as catalyst. Selective mono- or difluorination of oxalyl amide-protected benzylamine derivatives were achieved by modifying the reaction conditions, which presented an efficient method for the preparation of ortho-fluorinated benzylamines.

引用

页码：942 / 949

页数：8

共 50 条

[41] Palladium-Catalyzed C-H Acetoxylation Reations
Chen, Tianbao
Zhang, Ming
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (04) : 813 - 826
[42] Palladium-Catalyzed C-H ortho Arylation of Benzoic Acids with Diaryliodonium Salts in Water
Wu, Zhiqing
Chen, Si
Hu, Chenxu
Li, Zhengkai
Xiang, Haifeng
Zhou, Xiangge
CHEMCATCHEM, 2013, 5 (10) : 2839 - 2842
[43] Palladium-catalyzed electrophilic C-H fluorination of arenes using oxazoline as a removable directing group
Gutierrez, David A.
Lee, Wan-Chen Cindy
Shen, Yuning
Li, Jie Jack
TETRAHEDRON LETTERS, 2016, 57 (48) : 5372 - 5376
[44] Pd-Catalyzed Coupling of γ-C(sp3)-H Bonds of Oxalyl Amide-Protected Amino Acids with Heteroaryl and Aryl Iodides
Han, Jian
Zheng, Yongxiang
Wang, Chao
Zhu, Yan
Huang, Zhi-Bin
Shi, Da-Qing
Zeng, Runsheng
Zhao, Yingsheng
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (13): : 5681 - 5689
[45] Ruthenium-catalyzed meta/ortho-selective C-H alkylation of azoarenes using alkyl bromides
Li, Gang
Ma, Xingxing
Jia, Chunqi
Han, Qingqing
Wang, Ya
Wang, Junjie
Yu, Liuyang
Yang, Suling
CHEMICAL COMMUNICATIONS, 2017, 53 (07) : 1261 - 1264
[46] Palladium-Catalyzed Selective Benzylic C-H Alkylation of Aromatic Sulfonamides with Maleimides
Chakraborty, Trisha
Naskar, Gouranga
Jeganmohan, Masilamani
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (15): : 10624 - 10638
[47] Palladium-Catalyzed peri-Selective C-H Fluoroalkoxylation of Aryl Sulfoxides
Sato, Tomohiko
Nogi, Keisuke
Yorimitsu, Hideki
CHEMCATCHEM, 2020, 12 (13) : 3467 - 3471
[48] Ruthenium-Catalyzed Ortho-Selective C-H Alkenylation of Aromatic Compounds with Alkenyl Esters and Ethers
Ogiwara, Yohei
Tamura, Masaru
Kochi, Takuya
Matsuura, Yusuke
Chatani, Naoto
Kakiuchi, Fumitoshi
ORGANOMETALLICS, 2014, 33 (01) : 402 - 420
[49] Ruthenium-catalyzed Ortho-selective Aromatic C-H Silylation: Acceptorless Dehydrogenative Coupling of Hydrosilanes
Sakurai, Toru
Matsuoka, Yusuke
Hanataka, Tsurugi
Fukuyama, Naoaki
Namikoshi, Takeshi
Watanabe, Shinji
Murata, Miki
CHEMISTRY LETTERS, 2012, 41 (04) : 374 - 376
[50] Iridium-Catalyzed Ortho-Selective C-H Borylation of Aryl Ketones with Transient Imine Ligands
Liang, Min
Liu, Chuangchuang
Ju, Wenjie
Han, Shuxiong
Zhang, Jingyu
Zhao, Yingsheng
ORGANIC LETTERS, 2024, 26 (20) : 4224 - 4228

← 1 2 3 4 5 →