Palladium‐Catalyzed Selective Synthesis of Perfluoroalkylated Enynes from Perfluoroalkyl Iodides and Alkynes

An interesting palladium‐catalyzed procedure for the synthesis of perfluoroalkylated enynes from perfluoroalkyl iodides and alkynes was developed. The reaction proceeds through the addition of iodoperfluoroalkanes to terminal alkynes and subsequent Sonogashira coupling with the same alkynes. This tr...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-05, Vol.2017 (20), p.2940-2943
Main Authors: Qi, Xinxin, Ai, Han‐Jun, Cai, Chuang‐Xu, Peng, Jin‐Bao, Zheng, Feng, Wu, Xiao‐Feng
Format: Article
Language:English
Subjects:
Alkynes
Chemical synthesis
Compatibility
Coupling
Domino reactions
Efficiency
Enynes
Fluorinated compounds
Fluorine
Iodides
Palladium
Selectivity
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Summary:An interesting palladium‐catalyzed procedure for the synthesis of perfluoroalkylated enynes from perfluoroalkyl iodides and alkynes was developed. The reaction proceeds through the addition of iodoperfluoroalkanes to terminal alkynes and subsequent Sonogashira coupling with the same alkynes. This transformation could be conducted under mild reaction conditions with high efficiency and selectivity. Good functional group compatibility was observed, and a variety of perfluoroalkylated enynes products were isolated in good to excellent yields. An interesting palladium‐catalyzed procedure for the synthesis of perfluoroalkylated enynes from perfluoroalkyl iodides and alkynes is developed. The reaction proceeds under mild reaction conditions with high efficiency and selectivity. Good functional group compatibility is observed, and a variety of perfluoroalkylated enynes products are isolated in good to excellent yields. Rf = perfluoroalkyl group.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700642