Gold(I)-Catalyzed Tandem Cycloisomerization and Fluorination of 1,3(4)-Enyne Esters with NFSI: One-Pot Assembly of 5-Fluoro- Cyclopentenones

被引：20
作者：
Chen, Xianxiao [1 ]
Zhou, Yuanyuan [1 ]
Hong, Mei [1 ]
Ling, Yuan [1 ]
Yin, Dongliang [1 ]
Wang, Shifa [1 ]
Zhang, Xiaoxiang [1 ]
Rao, Weidong [1 ]
机构：
[1] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Key Lab Biomass Based Green Fuels & Chem, Nanjing 210037, Jiangsu, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 19期
基金：
中国国家自然科学基金;
关键词：
cycloisomerization; fluorination; 5-fluoro-cyclopentenones; gold; enyne esters; ALPHA-FLUOROKETONES; RAUTENSTRAUCH REARRANGEMENT; STEREOSELECTIVE-SYNTHESIS; GOLD CATALYSIS; DECARBOXYLATIVE FLUORINATION; N-FLUOROBENZENESULFONIMIDE; NUCLEOPHILIC FLUORINATION; BMS-204352 MAXIPOST(TM); DIAZOCARBONYL COMPOUNDS; MOLECULAR COMPLEXITY;
D O I：
10.1002/adsc.201800701
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient synthetic approach for the synthesis of 5-fluoro-cyclopentenones containing a fluorine-substituted carbon stereocenter that relies on gold(I)-catalyzed cycloisomerization and fluorination sequence of 1,3(4)-enyne esters with N-fluorbenzensulfonimide (NFSI) is described. This tandem transformation exhibited a broad substrate scope and excellent functional group compatibility, providing a novel protocol for rapid assembly 5-fluoro-cyclopentenones in good to excellent yields under mild reaction conditions. The mechanistic studies revealed that the transformation involves a gold-catalyzed cycloisomerization and electrophilic fluorination cascade to give the 5-fluoro-cyclopentenones.
引用
收藏
页码：3700 / 3708
页数：9
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