Stereoselective Synthesis of (Z)-β-Enamido Triflates and Fluorosulfonates from N-Fluoroalkylated Triazoles

被引：28

作者：

Markos, Athanasios ^{[1
,2
]}

Voltrova, Svatava ^{[1
]}

Motornov, Vladimir ^{[1
,3
]}

Tichy, David ^{[1
]}

Klepetarova, Blanka ^{[1
]}

Beier, Petr ^{[1
]}

机构：

[1] Czech Acad Sci, Inst Organ Chem & Biochem, Flemingovo Nam 2, Prague 16610 6, Czech Republic

[2] Charles Univ Prague, Dept Organ Chem, Fac Sci, Hlavova 2030-8, Prague 12843 2, Czech Republic

[3] DI Mendeleev Univ Chem Technol Russia, Higher Chem Coll, Miusskaya Sq 9, Moscow 125047, Russia

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 32期

关键词：

1,2,3-triazoles; enamides; triazolium salts; vinyl cations; vinyl triflates; TERMINAL ALKYNES; VINYL CATIONS; SOLVOLYSIS; AZIDES; CYCLOADDITION; DERIVATIVES; MECHANISM; ARYLATION; ENAMIDES; ESTERS;

D O I：

10.1002/chem.201901632

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Fluoroalkylated 1,2,3-triazoles in the presence of triflic acid or fluorosulfonic acid underwent a cascade reaction consisting of triazole protonation, ring opening, nitrogen elimination, sulfonate addition, HF elimination, and hydrolysis to furnish novel trifluoromethanesulfonyloxy- or fluorosulfonyloxy-substituted enamides, respectively, in a highly stereoselective fashion. The vinyl triflates underwent cross-coupling reactions to a variety of substituted enamides and serve as sources of the aminovinyl cations. In reactions with triflic acid, electron-rich triazoles afforded 2-fluoroalkylated oxazoles.

引用

页码：7640 / 7644

页数：5

共 57 条

[1] Zinc(II) Catalyzed Conversion of Alkynes to Vinyl Triflates in the Presence of Silyl Triflates [J].

Al-huniti, Mohammed H. ;

Lepore, Salvatore D. .

ORGANIC LETTERS, 2014, 16 (16) :4154-4157

[2]

[Anonymous], ANGEW CHEM

[3]

[Anonymous], 2018, ANGEW CHEM, V130, P17186

[4] PERFLUOROALKYL DERIVATIVES OF NITROGEN .4. THE SYNTHESIS, PROPERTIES AND INFRARED SPECTRA OF PERFLUOROALKYL ISOCYANATES AND CARBAMATES [J].

BARR, DA ;

HASZELDINE, RN .

JOURNAL OF THE CHEMICAL SOCIETY, 1956, (SEP) :3428-3435

[5] Synthesis of phthalan and phenethylamine derivatives via addition of alcohols to rhodium(II)-azavinyl carbenoids [J].

Bennett, John M. ;

Shapiro, Jonathan D. ;

Choinski, Krystina N. ;

Mei, Yingbin ;

Aulita, Sky M. ;

Reinheimer, Eric W. ;

Majireck, Max M. .

TETRAHEDRON LETTERS, 2017, 58 (12) :1117-1122

[6]

Blastik Z. E., 2017, ANGEW CHEM, V129, P352

[7] 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

[8] Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides [J].

Cassidy, Michael P. ;

Raushel, Jessica ;

Fokin, Valery V. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) :3154-3157

[9] Stereoselective 1,3-Insertions of Rhodium(II) Azavinyl Carbenes [J].

Chuprakov, Stepan ;

Worrell, Brady T. ;

Selander, Nicklas ;

Sit, Rakesh K. ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (01) :195-202

[10] Reactivity Profiles of Diazo Amides, Esters, and Ketones in Transition-Metal-Free C-H Insertion Reactions [J].

Cleary, Sarah E. ;

Li, Xin ;

Yang, Li-Cheng ;

Houk, K. N. ;

Hong, Xin ;

Brewer, Matthias .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (08) :3558-3565

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