Copper-Catalyzed Oxidative Perfluoroalkylation of Aryl Boronic Acids Using Perfluoroalkylzinc Reagents

被引：19

作者：

Bao, Xifei ^{[1
]}

Liu, Lihua ^{[2
]}

Li, Junlan ^{[1
]}

Fan, Shilu ^{[1
]}

机构：

[1] Hefei Univ Technol, Sch Chem & Chem Engn, 193 Tunxi Rd, Hefei 230000, Anhui, Peoples R China

[2] Hefei Univ Technol, Sch Biol & Med Engn, 193 Tunxi Rd, Hefei 230000, Anhui, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 01期

基金：

中国国家自然科学基金;

关键词：

CROSS-COUPLING REACTIONS; C-H PERFLUOROALKYLATION; REDUCTIVE ELIMINATION; TRIFLUOROMETHYLATION; ARENES; FLUORINATION; CHEMISTRY; IODIDES; PALLADIUM; CUPRATION;

D O I：

10.1021/acs.joc.7b02557

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and synthetically convenient method for copper-catalyzed cross-coupling of aryl boronic acids with perfluoroalkyl zinc reagents has been described. The reaction proceeds under mild reaction conditions with a high efficiency and broad substrate scope and provides a general access to perfluoroalkylated arenes, which are of interest in life and materials science.

引用

页码：463 / 468

页数：6

共 61 条

[1] Stable but Reactive Perfluoroalkylzinc Reagents: Application in Ligand-Free Copper-Catalyzed Perfluoroalkylation of Aryl Iodides [J].

Aikawa, Kohsuke ;

Nakamura, Yuzo ;

Yokota, Yuki ;

Toya, Wataru ;

Mikami, Koichi .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (01) :96-100

[2] Aryl-CF3 Bond-Forming Reductive Elimination from Palladium(IV) [J].

Ball, Nicholas D. ;

Kampf, Jeff W. ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) :2878-+

[3] Perfluoroalkylation reactions of (hetero)arenes [J].

Barata-Vallejo, Sebastian ;

Bonesi, Sergio M. ;

Postigo, Al .

RSC ADVANCES, 2015, 5 (77) :62498-62518

[4] Heterogeneous Photoinduced Homolytic Aromatic Substitution of Electron-Rich Arenes with Perfluoroalkyl Groups in Water and Aqueous Media - A Radical-Ion Reaction [J].

Barata-Vallejo, Sebastian ;

Martin Flesia, Marina ;

Lantano, Beatriz ;

Argueello, Juan E. ;

Penenory, Alicia B. ;

Postigo, Al .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (05) :998-1008

[5] Photocatalytic/Cu-Promoted C-H Activations: Visible-light-Induced ortho-Selective Perfluoroalkylation of Benzamides [J].

Chen, Xiang ;

Tan, Ze ;

Gui, Qingwen ;

Hu, Liang ;

Liu, Jidan ;

Wu, Jing ;

Wang, Guangwei .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (18) :6218-6222

[6] Oxidative Trifluoromethylation and Trifluoromethylthiolation Reactions Using (Trifluoromethyl)trimethylsilane as a Nucleophilic CF3 Source [J].

Chu, Lingling ;

Qing, Feng-Ling .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) :1513-1522

[7] Copper-Catalyzed Direct C-H Oxidative Trifluoromethylation of Heteroarenes [J].

Chu, Lingling ;

Qing, Feng-Ling .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) :1298-1304

[8] Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids [J].

Chu, Lingling ;

Qing, Feng-Ling .

ORGANIC LETTERS, 2010, 12 (21) :5060-5063

[9] Copper-Mediated Aerobic Oxidative Trifluoromethylation of Terminal Alkynes with Me3SiCF3 [J].

Chu, Lingling ;

Qing, Feng-Ling .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7262-+

[10] Active trifluoromethylating agents from well-defined copper(I)-CF3 complexes [J].

Dubinina, Galyna G. ;

Furutachi, Hideki ;

Vicic, David A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) :8600-+

← 1 2 3 4 5 6 7 →