Palladium-Catalyzed Tandem Fluorination and Cyclization of Enynes

被引:85
|
作者
Peng, Haihui [1 ]
Liu, Guosheng [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
关键词
ARYL FLUORIDES; BOND FORMATION; STEREOSELECTIVE-SYNTHESIS; METAL CATALYSIS; ALKYNES; REACTIVITY; CONVERSION; MOLECULES; STATE;
D O I
10.1021/ol103039x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel palladium-catalyzed tandem fluorination and cyclization of enynes has been developed. A favorable cis-fluoropalladation is proposed as a key step to construct a vinyl-F bond, and the final C-5p3-Pd bond is reduced by alcohol. This transformation represents an efficient road to synthesize fluorinated lactams.
引用
收藏
页码:772 / 775
页数:4
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