Silver-catalyzed monofluoroalkylation of heteroarenes with α-fluorocarboxylic acids: an insight into the solvent effect

被引：17

作者：

Guo, Chunfang ^{[1
,2
]}

Liu, Zhaolong ^{[1
]}

Li, Xiangye ^{[1
]}

Han, Xuliang ^{[1
]}

Li, Yueyun ^{[1
]}

Liu, Hui ^{[1
]}

Zhang, Lizhi ^{[1
]}

Li, Xinjin ^{[1
,3
]}

Dong, Yunhui ^{[1
]}

机构：

[1] Shandong Univ Technol, Coll Chem & Chem Engn, 266 West Xincun Rd, Zibo 255000, Peoples R China

[2] Shandong Vocat Coll Light Ind, Zhoucun Mishan Rd, Zibo 255300, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2022年 / 58卷 / 08期

关键词：

C-H TRIFLUOROMETHYLATION; FLUORINE; DIFLUOROMETHYLATION; PHARMACEUTICALS; ARENES;

D O I：

10.1039/d1cc06466e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A mild and efficient method for direct C-H monofluoroalkylation of heteroarenes with easily accessible and inexpensive alpha-fluorocarboxylic acids has been developed. This silver-catalyzed reaction affords mono- and bis-monofluoroalkylated heteroarenes in good yields under mild conditions, and the solvent effect on the monofluoroalkylation reaction is discussed in detail.

引用

页码：1147 / 1150

页数：4

共 45 条

[11] Direct Copper-Catalyzed C-H Monofluoroalkylation of Benzoxazoles with 1-Fluoro-1-haloalkanes [J].

Li, Wei ;

Varenikov, Andrii ;

Gandelman, Mark .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (21) :3138-3141

[12] Recent advance in the synthesis of (1,1-difluoroethyl)arenes [J].

Li, Xinjin ;

Liu, Jianchang ;

Li, Xiangye ;

Liu, Hefu ;

Liu, Hui ;

Li, Yueyun ;

Liu, Yuying ;

Dong, Yunhui .

JOURNAL OF FLUORINE CHEMISTRY, 2018, 216 :102-106

[13] Nickel-Catalyzed Coupling Reaction of α-Bromo-α-fluoroketones with Arylboronic Acids toward the Synthesis of α-Fluoroketones [J].

Liang, Junqing ;

Hang, Jie ;

Wu, Jingjing ;

Wu, Pingjie ;

Hu, Jian ;

Hu, Feng ;

Wu, Fanhong .

ORGANIC LETTERS, 2019, 21 (17) :6844-6849

[14] Introduction of Fluorine and Fluorine-Containing Functional Groups [J].

Liang, Theresa ;

Neumann, Constanze N. ;

Ritter, Tobias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (32) :8214-8264

[15] Photo-driven redox-neutral decarboxylative carbon-hydrogen trifluoromethylation of (hetero)arenes with trifluoroacetic acid [J].

Lin, Jin ;

Li, Zhi ;

Kan, Jian ;

Huang, Shijun ;

Su, Weiping ;

Li, Yadong .

NATURE COMMUNICATIONS, 2017, 8

[16] Cobalt-Catalyzed α-Arylation of Substituted α-Bromo α-Fluoro β-Lactams with Diaryl Zinc Reagents: Generalization to Functionalized Bromo Derivatives [J].

Lorion, Melanie M. ;

Koch, Vanessa ;

Nieger, Martin ;

Chen, Hi-Yung ;

Lei, Aiwen ;

Braese, Stefan ;

Cossy, Janine .

CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (58) :13163-13169

[17] Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design [J].

Meanwell, Nicholas A. .

JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (14) :5822-5880

[18] Fluorine in pharmaceuticals:: Looking beyond intuition [J].

Mueller, Klaus ;

Faeh, Christoph ;

Diederich, Francois .

SCIENCE, 2007, 317 (5846) :1881-1886

[19] Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis [J].

Nagib, David A. ;

MacMillan, David W. C. .

NATURE, 2011, 480 (7376) :224-228

[20] The unique fluorine effects in organic reactions: recent facts and insights into fluoroalkylations [J].

Ni, Chuanfa ;

Hu, Jinbo .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (20) :5441-5454

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