Copper(0)-mediated fluoroalkylation of iodobenzene with 2-bromo-1,1,2,2-tetrafluoroethyl compounds: Investigation on the influence of R substituent on the reactivity of RCF2Cu species

被引：32

作者：

Zhu, Jieming ^{[1
]}

Ni, Chuanfa ^{[1
]}

Gao, Bing ^{[1
]}

Hu, Jinbo ^{[1
]}

机构：

[1] Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2015年 / 171卷

基金：

中国国家自然科学基金;

关键词：

Fluoroallcylation; Copper; Cross-coupling; Tatrafluoroethylenation; ARYLBORONIC ACIDS; COPPER; TRIFLUOROMETHYLATION; ROUTE; PENTAFLUOROETHYLATION; ARYLATION;

D O I：

10.1016/j.jfluchem.2014.08.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

We have made a systematic investigation on the copper(0)-mediated tetrafluoroethylenation of iodobenzene with structurally diverse 2-bromo-1,1,2,2-tetrafluoroethyl compounds. A comparison of this reaction with 1,2,2-trifluoro-1-phenylethylation and the known functionalized difluoroalkylation demonstrates that the substituent R of alpha,alpha-difluoroalkyl copper species RCF2Cu plays a crucial role on their reactivity, which is believed to be useful for the development of new fluoroalkylation reactions under the promotion of transition metals. (C) 2014 Elsevier B.V. All rights reserved.

引用

页码：139 / 147

页数：9

共 55 条

[11] Palladium-Catalyzed Difluoroalkylation of Aryl Boronic Acids: A New Method for the Synthesis of Aryldifluoromethylated Phosphonates and Carboxylic Acid Derivatives [J].

Feng, Zhang ;

Min, Qiao-Qiao ;

Xiao, Yu-Lan ;

Zhang, Bo ;

Zhang, Xingang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (06) :1669-1673

[12] A New Method for Aromatic Difluoromethylation: Copper-Catalyzed Cross-Coupling and Decarboxylation Sequence from Aryl Iodides [J].

Fujikawa, Kenichi ;

Fujioka, Yasutaka ;

Kobayashi, Akira ;

Amii, Hideki .

ORGANIC LETTERS, 2011, 13 (20) :5560-5563

[13] Selective Incorporation of Difluoromethylene Moieties into Arenes Assisted by Transition Metals [J].

Gao, Bing ;

Ni, Chuanfa ;

Hu, Jinbo .

CHIMIA, 2014, 68 (06) :414-418

[14] Direct addition of fluorine to arylacetylenes [J].

Gatenyo, Julia ;

Rozen, Shlomo .

JOURNAL OF FLUORINE CHEMISTRY, 2009, 130 (03) :332-335

[15] Pd-Catalyzed α-Arylation of α,α-Difluoroketones with Aryl Bromides and Chlorides. A Route to Difluoromethylarenes [J].

Ge, Shaozhong ;

Chaladaj, Wojciech ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (11) :4149-4152

[16]

Hafner A, 2014, SYNTHESIS-STUTTGART, V46, P1440, DOI 10.1055/s-0033-1341223

[17] THE CHEMISTRY OF SULFUR TETRAFLUORIDE .2. THE FLUORINATION OF ORGANIC CARBONYL COMPOUNDS [J].

HASEK, WR ;

SMITH, WC ;

ENGELHARDT, VA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (03) :543-551

[18]

Inbasekaran M.N., 1988, [No title captured], Patent No. [US 4,870,213, 4870213]

[19] Copper-mediated difluoromethylation of electron-poor aryl iodides at room temperature [J].

Jiang, Xue-Liang ;

Chen, Zeng-Hao ;

Xu, Xiu-Hua ;

Qing, Feng-Ling .

ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (07) :774-776

[20] Nematic liquid crystals with a tetrafluoroethylene bridge in the mesogenic core structure [J].

Kirsch, P ;

Bremer, M ;

Huber, F ;

Lannert, H ;

Ruhl, A ;

Lieb, M ;

Wallmichrath, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (23) :5414-5417

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