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

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