Chemoselective Aza-[4+3]-annulation of N-Perfluoroalkyl-1,2,3-triazoles with 1,3-Dienes: Access to N-Perfluoroalkyl-Substituted Azepines

被引：44

作者：

Motornov, Vladimir ^{[1
,2
]}

Beier, Petr ^{[1
]}

机构：

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

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 24期

关键词：

RHODIUM-CATALYZED TRANSANNULATION; 1,2,3-TRIAZOLES; REARRANGEMENT; GENERATION; ANNULATION; FLUORINE; ALKYNES; AZIDES;

D O I：

10.1021/acs.joc.8b02472

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium-catalyzed transannulation of N-perfluoroalkylated 1,2,3-triazoles with 1,3-dienes under microwave heating proceeded chemoselectively via the formal aza-[4+3]-pathway, affording N-perfluoroalkyl-substituted 2,5-dihydroazepines. A unique regioselectivity profile was observed in annulation with 1-substituted 1,3-diene, affording unusual 5,6-disubstituted examples. Transannulation of triazoles with 2-trimethylsilyloxybutadiene provided N-perfluoroalkyl-substituted azepinone derivatives.

引用

页码：15195 / 15201

页数：7

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