Synthesis of fluorinated 3-pyrrolines and pyrroles via [3+2] annulation of N-aryl fluorinated imines with allenoates catalyzed by phosphine

被引：16

作者：

Zhu, Zhentong ^{[1
,2
]}

Guo, Yuwei ^{[2
,3
]}

Wang, Xiaojun ^{[2
,3
]}

Wu, Fanhong ^{[1
]}

Wu, Yongming ^{[2
]}

机构：

[1] Shanghai Inst Technol, Sch Chem & Environm Engn, 100 Haiquan Rd, Shanghai 201418, Peoples R China

[2] Shanghai Inst Organ Chem, Key Lab Organolluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

[3] Shanghai Univ, Dept Chem, 99 Shangda Rd, Shanghai 200444, Peoples R China

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2017年 / 195卷

基金：

中国国家自然科学基金;

关键词：

Fluorinated pyrrole; Fluorinated; 3-pyrroline; N-aryl fluorinated imines; Allenoates; 3+2] annulation; RING-CLOSING METATHESIS; NITROGEN-HETEROCYCLES; CYCLOADDITION; CHEMISTRY; 2,3-BUTADIENOATES; AROMATIZATION; 2-BUTYNOATES; ALKALOIDS; ALKENES; OLEFINS;

D O I：

10.1016/j.jfluchem.2016.12.010

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A phosphine-catalyzed [3 + 2] annulation of N-aryl fluorinated imines with allenoates is reported. A series of fluorinated pyrrolines is obtained in moderate yield, which are further transformed to fluorinated pyrroles via dehydro-aromatization by DDQ in high to excellent yield. The reaction mechanism is also discussed. (C) 2016 Published by Elsevier B.V.

引用

页码：102 / 107

页数：6

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