Intramolecular Construction of Trifluoromethyl Group by the Palladium-Catalyzed Alkylation of 2,3,3-Trifluoroallylic Carbonates with Indoles

被引:15
|
作者
Hanakawa, Taisyun [1 ]
Isa, Kazuki [1 ]
Isobe, Shin-ichi [1 ]
Hoshino, Yuji [1 ]
Zhou, Biao [1 ]
Kawatsura, Motoi [1 ]
机构
[1] Nihon Univ, Coll Humanities & Sci, Dept Chem, Setagaya Ku, Tokyo 1568550, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 04期
基金
日本学术振兴会;
关键词
1,3-DISUBSTITUTED ALLYLIC ESTERS; REGIOSELECTIVE SYNTHESIS; MEDICINAL CHEMISTRY; NUCLEOPHILIC-ATTACK; FLUORINE; AMINATION; ACETATES; CYCLOPROPANATION; PHARMACEUTICALS; DERIVATIVES;
D O I
10.1021/acs.joc.6b03085
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalyzed alkylation reaction of 2,3,3-trifluoroallylic carbonates with indoles afforded a trifluoromethyl group possessing 3-substituted indole derivatives. The reaction proceeded via attack of the C-3 carbon of the indoles onto the C-2 position of the allylic moiety and intramolecular construction of the trifluoromethyl group by the intramolecular fluorine atom shift from the C-2 position to the C-3 position of the allyl unit.
引用
收藏
页码:2281 / 2287
页数:7
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