Difluoroacetic Acid as a New Reagent for Direct C-H Difluoromethylation of Heteroaromatic Compounds

被引：84

作者：

Truong Thanh Tung ^{[1
]}

Christensen, Soren Brogger ^{[1
]}

Nielsen, John ^{[1
]}

机构：

[1] Univ Copenhagen, Dept Drug Design & Pharmacol, Univ Pk 2, DK-2100 Copenhagen, Denmark

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 72期

关键词：

difluoroacetic acid; difluoromethylation; drug discovery; fluorine; radicals; COPPER-MEDIATED DIFLUOROMETHYLATION; CROSS-COUPLING REACTION; CATALYZED DIFLUOROMETHYLATION; (DIFLUOROMETHYL)ZINC REAGENT; DECARBOXYLATIVE FLUORINATION; MEDICINAL CHEMISTRY; ARYLBORONIC ACIDS; ARYL HALIDES; DRUG DESIGN; IODIDES;

D O I：

10.1002/chem.201704261

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A technically simple procedure for direct C-H difluoromethylation of heteroaromatic compounds using off-the-shelf difluoroacetic acid as the difluoromethylating reagent has been developed. Mono-difluoromethylation versus bis-difluoromethylation is controlled as the result of the reaction temperature. The reactions described here enable access to the late-stage C-H mono- and bis-difluoromethylation for preparation of tool compounds for chemical biology and provide access to this hitherto untapped substituent for drug discovery.

引用

页码：18125 / 18128

页数：4

共 50 条

[41] A New Entry of Amination Reagents for Heteroaromatic C-H Bonds: Copper-Catalyzed Direct Amination of Azoles with Chloroamines at Room Temperature
Zanda, Matteo
SYNTHESIS-STUTTGART, 2010, (15): : A68 - A69
[42] A New Way to Transform C-H Bonds into Complex Compounds
不详
CHEMPHYSCHEM, 2012, 13 (04) : 899 - 899
[43] Direct C–H difluoromethylation of heterocycles via organic photoredox catalysis
Wei Zhang
Xin-Xin Xiang
Junyi Chen
Chen Yang
Yu-Liang Pan
Jin-Pei Cheng
Qingbin Meng
Xin Li
Nature Communications, 11
[44] Nickel-Catalyzed Direct C-H Trifluoromethylation of Free Anilines with Togni's Reagent
Gao, Xianying
Geng, Yang
Han, Shuaijun
Liang, Apeng
Li, Jingya
Zou, Dapeng
Wu, Yusheng
Wu, Yangjie
ORGANIC LETTERS, 2018, 20 (13) : 3732 - 3735
[45] Direct C-H amination and C-H chloroamination of 7-deazapurines
Sabat, Nazarii
Klecka, Martin
Slavetinska, Lenka
Klepetarova, Blanka
Hocek, Michal
RSC ADVANCES, 2014, 4 (107) : 62140 - 62143
[46] Direct C-H Cyanoalkylation of Heteroaromatic N-Oxides and Quinones via C-C Bond Cleavage of Cyclobutanone Oximes
Gu, Yu-Rui
Duan, Xin-Hua
Yang, Lin
Guo, Li-Na
ORGANIC LETTERS, 2017, 19 (21) : 5908 - 5911
[47] A Direct Approach to Decoration of Bioactive Compounds via C-H Amination Reaction
Ju, Guodong
Yuan, Chunchen
Wang, Dongjie
Zhang, Jingyu
Zhao, Yingsheng
ORGANIC LETTERS, 2019, 21 (24) : 9852 - 9855
[48] Promoting Photocatalytic Direct C-H Difluoromethylation of Heterocycles using Synergistic Dual-Active-Centered Covalent Organic Frameworks
Li, Sizhe
Wei, Wenxin
Chi, Kai
Ferguson, Calum T. J.
Zhao, Yan
Zhang, Kai A. I.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (18) : 12386 - 12394
[49] Ruthenium-Catalyzed Meta-Selective C-H Difluoromethylation of Phenol Derivatives
Xu, Xu
Tao, Na
Fan, Wei-Tai
Tu, Guangliang
Geng, Jingyao
Zhang, Jingyu
Zhao, Yingsheng
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (21): : 13868 - 13876
[50] The direct C-H halogenations of indoles
Shi, Leilei
Zhang, Dongmei
Lin, Riyuan
Zhang, Chun
Li, Xun
Jiao, Ning
TETRAHEDRON LETTERS, 2014, 55 (14) : 2243 - 2245

← 1 2 3 4 5 →