Synthesis of tetrafluoroethylene- and tetrafluoroethyl-containing azides and their 1,3-dipolar cycloaddition as synthetic application

被引:33
作者
Voltrova, Svatava [1 ]
Muselli, Mickael [1 ]
Filgas, Josef [1 ]
Matousek, Vaclav [2 ]
Klepetarova, Blanka [1 ]
Beier, Petr [1 ]
机构
[1] Czech Acad Sci, Inst Organ Chem & Biochem, Flemingovo Namesti 2, Prague 16610, Czech Republic
[2] CF Plus Chem Sro, Kamenice 771-34, Brno 62500, Czech Republic
关键词
NUCLEOPHILIC TETRAFLUOROETHYLATION; ALKYNE CYCLOADDITION; LIQUID-CRYSTALS; TRIFLUOROMETHYLATION; ALPHA; ALPHA-DIFLUOROAZIDES; PERFLUOROALKYLATION; FLUOROALKYLATION; FLUORINATION; DERIVATIVES; CHEMISTRY;
D O I
10.1039/c7ob01151b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tetrafluoroethylene-containing azides are accessed in two steps (one pot) from tetrafluoroalkyl bromides by metalation and reaction with electrophilic azides. Subsequent copper(I)-catalyzed azide-alkyne cycloaddition afforded N-tetrafluoroethyl and N-tetrafluoroethylene 4-substituted 1,2,3-triazoles. In addition, the protocol for the synthesis of 4,5-disubstituted 1,2,3-triazoles is presented.
引用
收藏
页码:4962 / 4965
页数:4
相关论文
共 48 条
[1]   Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes [J].
Alonso, Concepcion ;
Martinez de Marigorta, Eduardo ;
Rubiales, Gloria ;
Palacios, Francisco .
CHEMICAL REVIEWS, 2015, 115 (04) :1847-1935
[2]   SYNTHESIS OF FLUORO NITRO ETHERS BY MICHAEL ADDITION-REACTIONS TO ACTIVATED BETA,BETA-DIFLUOROOLEFINS [J].
ARCHIBALD, TG ;
BAUM, K .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) :3562-3565
[3]   CHEMOENZYMATIC SYNTHESIS AND BIOLOGICAL-ACTIVITY OF BOTH ENANTIOMERIC FORMS OF TETRACONAZOLE, A NEW ANTIFUNGAL TRIAZOLE [J].
BIANCHI, D ;
CESTI, P ;
SPEZIA, S ;
GARAVAGLIA, C ;
MIRENNA, L .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1991, 39 (01) :197-201
[4]   Azidoperfluoroalkanes: Synthesis and Application in Copper(I)-Catalyzed Azide-Alkyne Cycloaddition [J].
Blastik, Zsofia E. ;
Voltrova, Svatava ;
Matousek, Vaclav ;
Jurasek, Bronislav ;
Manley, David W. ;
Klepetarova, Blanka ;
Beier, Petr .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (01) :346-349
[5]   Enantioselective synthesis of tetrafluoroethylene-containing monosaccharides [J].
Boydell, AJ ;
Vinader, V ;
Linclau, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (42) :5677-5679
[6]   Nucleophilic Tetrafluoroethylation Employing in Situ Formed Organomagnesium Reagents [J].
Budinska, Alena ;
Vaclavik, Jiri ;
Matousek, Vaclav ;
Beier, Petr .
ORGANIC LETTERS, 2016, 18 (22) :5844-5847
[7]   Synthesis of tetrafluoroethyl- and tetrafluoroethylene-containing amines by the reaction of silanes with enamines under acidic conditions [J].
Chernykh, Yana ;
Jurasek, Bronislav ;
Beier, Petr .
JOURNAL OF FLUORINE CHEMISTRY, 2015, 171 :162-168
[8]   Development of (2-bromo-1,1,2,2-tetrafluoroethyl)(phenyl)sulfane as tetrafluoroethyl-radical and tetrafluoroethylene-diradical synthons for additions to alkenes [J].
Chernykh, Yana ;
Beier, Petr .
JOURNAL OF FLUORINE CHEMISTRY, 2013, 156 :307-313
[9]   Development of PhSCF2CF2SiMe3 as a Tandem Anion and Radical Tetrafluoroethylene Equivalent: Preparation of Tetrafluoroethyl-Substituted Alcohols and Tetrafluorotetrahydropyrans [J].
Chernykh, Yana ;
Hlat-Glembova, Katarina ;
Klepetarova, Blanka ;
Beier, Petr .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (24) :4528-4531
[10]   PROPERTIES OF AZIDOTRIFLUOROMETHANE [J].
CHRISTE, KO ;
SCHACK, CJ .
INORGANIC CHEMISTRY, 1981, 20 (08) :2566-2570