The introduction of polyfluoroalkyl groups into organic molecules can bring some dramatic changes, which have been recognized as an important tool in improving physical properties, chemical reactivities and biological activities.[1] To enrich the methods available for the synthesis of perfluoroalkyl-substituted compounds and potentially promote their application are our main tasks and responsibilities.[2] A convenient strategy for producing polyfluoroalkylated compounds is the preparation and application of ?uorine-containing building blocks.[3] However, what most interests us among these ?uorine-containing building blocks is electron-deficient alkyne like perfluoroalk-2-ynoate. Recently, we mainly focus on using methyl perfluoroalk-2-ynoates as fluorinated building block through the cuprous-mediated coupling-cyclization of anilines to produce varied kinds of quinoline or indole derivatives (Scheme 1). All reactions proceed smooth under relative mild condition, which made the transformation sustainable and practical.[4] Thanks are due to the National Natural Science Foundation of China (Grant Nos. 21072126, 21272152) for the financial support.References: [1] (a) Banks, R. E.; Smart, B. E.; Tatlow, J. C. Organofluorine Chemistry: Principles and Commercial Applications, Plenum Press, New York, 1994  ; (b) Filler, R.; Kobayashi, Y.; Yagupolskii, L. M. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, Elsevier, Amsterdam, 1993 .[2] Thayer, A. M. Chem. Eng. New 2006  , 84, 15.[3] Peng, W. M.; Zhu, S. Z. Acta Chimica Sinica 2003  , 61, 455.[4] (a) Han, J.; Cao, L.; Bian, L. Chen, J; Deng, H.; Shao, M.; Jin, Z.; Zhang, H.; Cao, W. Adv. Synth. Catal.2013  , 355, 1345-1350; (b) Han, J.; Li, L.; Shen, Y.; Chen, J.; Deng, H.; Shao, M.; Lu, X.; Zhang, H.; Cao, W. Eur. J. Org. Chem. Submitted.

Cu(I)-catalyzed coupling cyclization of methyl perfluoroalk-2-ynoates

247th National Meeting (2014)

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