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

[1] Formation and structure of a fluorinated [2.2]paracyclophan-1-ene
Amii, Hideki
Hayashi, Ryotaro
Seo, Motoharu
Katahira, Yukako
Kobayashi, Akira
Uneyama, Kenji
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2013, 152 : 90 - 93
[2] The Trifluoromethyl Group in Transition Metal Chemistry
Angeles Garcia-Monforte, M.
Martinez-Salvador, Sonia
Menjon, Babil
[J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2012, (31) : 4945 - 4966
[3] A highly efficient room temperature non-organometallic route for the synthesis of α,β,β-trifluorostyrenes by dehydrohalogenation
Anilkumar, R
Burton, DJ
[J]. TETRAHEDRON LETTERS, 2003, 44 (35) : 6661 - 6664
[4] [Anonymous], 2013, MODERN FLUOROORGANIC
[5] FLUORINATED ORGANOMETALLICS - PERFLUOROALKYL AND FUNCTIONALIZED PERFLUOROALKYL ORGANOMETALLIC REAGENTS IN ORGANIC-SYNTHESIS
BURTON, DJ
YANG, ZY
[J]. TETRAHEDRON, 1992, 48 (02) : 189 - 275
[6] Oxidative Trifluoromethylation and Trifluoromethylthiolation Reactions Using (Trifluoromethyl)trimethylsilane as a Nucleophilic CF3 Source
Chu, Lingling
Qing, Feng-Ling
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) : 1513 - 1522
[7] Dolbier Jr W.R., 2009, GUIDE FLUORINE NMR O, P126
[8] Parylene-AF4: a polymer with exceptional dielectric and thermal properties
Dolbier, WR
Beach, WF
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2003, 122 (01) : 97 - 104
[9] A NEW SYNTHESIS OF OCTAFLUORO[2.2]PARACYCLOPHANE
DOLBIER, WR
ASGHAR, MA
PAN, HQ
CELEWICZ, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) : 1827 - 1830
[10] Exploring trifluoromethylation reactions at nickel: A structural and reactivity study
Dubinina, Galyna G.
Brennessel, William W.
Miller, Jennifer L.
Vicic, David A.
[J]. ORGANOMETALLICS, 2008, 27 (15) : 3933 - 3938

← 1 2 3 4 5 6 →