Synthesis of 2,2,2-Trifluoroethyl Oxazoles, Oxazolines and Furans via Alkyne Oxytrifluoromethylation

被引：21
作者：
Dong, Jia-Jia [1 ]
Zhang, Song-Lin [1 ]
机构：
[1] Jiangnan Univ, Sch Chem & Mat Engn, Key Lab Synthet & Biol Colloids, Minist Educ, Wuxi 214122, Jiangsu, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 04期
基金：
中国国家自然科学基金;
关键词：
Trifluoromethylation; Cu(III)-CF3 compounds; dual functionalization; oxytrifluoromethylation; oxazoles preparation; CROSS-COUPLING REACTIONS; C-H TRIFLUOROETHYLATION; TRIFLUOROMETHYL COMPLEXES; EFFICIENT SYNTHESIS; COPPER; CONSTRUCTION; INTERMEDIATE; FLUORINE; ALKENES; ACCESS;
D O I：
10.1002/adsc.201901405
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
This study reports an oxytrifluoromethylation method for construction of oxazoles and furans motif and the concurrent incorporation of a 2,2,2-trifluoroethyl group at the aromatic C5-position. High-valent copper(III) trifluoromethyl compounds are crucial to this reaction that induces oxy-trifluoromethylation of alkynes with a pendant amide/enol group functioning as the oxygen-nucleophile. A wide substrate scope is demonstrated with high efficiency and with broad functional group tolerance. Late-stage functionalization of dehydrocholic acid, a complex drug compound, is accomplished to show the potential of this method for practical drug design.
引用
收藏
页码：795 / 800
页数：6
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