Silver-Catalyzed Regioselective Synthesis of Highly Substituted 2-Trifluoromethyl Pyrroles

被引：16
|
作者：
Wu, Wei [1 ]
Wen, Shunli [2 ]
Zhang, Xinyu [2 ]
Lin, Qi [1 ]
Weng, Zhiqiang [1 ]
机构：
[1] Minjiang Univ, Ocean Coll, Fujian Engn Res Ctr New Chinese Iacquer Mat, Fuzhou 350108, Peoples R China
[2] Fuzhou Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fujian 350108, Peoples R China
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 16期
基金：
中国国家自然科学基金;
关键词：
VINYL AZIDES; TRIFLUOROMETHYLATION; FLUORINE; COPPER;
D O I：
10.1021/acs.orglett.1c02136
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient and regioselective synthesis of highly substituted 2-trifluoromethyl pyrrole derivatives via silver-catalyzed cyclization of vinyl azides with ethyl 4,4,4-trifluoro-3-oxobutanoate is reported. Various alpha-(heteo)aryl, alkyl, alpha-aryl, as well as alpha,beta-disubstituted vinyl azides, participate in this transformation. The reaction mechanism likely involves the addition of in situ generated 2H-azirine to the diketone species, followed by intramolecular addition, N-C-1 cleavage, and elimination.
引用
收藏
页码：6352 / 6356
页数：5
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