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DOI: 10.1055/s-0030-1258611
Copper-Catalyzed Annulative Synthesis of 2-Fluoromethylated Quinolines
S. Li, Y. Yuan, J. Zhu, H. Xie, Z. Chen, Y. Wu*
Shanghai Institute of Organic Chemistry and Huazhong University of Science and Technology, Wuhan, P. R. of China
Publication History
Publication Date:
22 September 2010 (online)
Significance
Reported is the synthesis of 2-fluoromethylated quinolines through a copper-catalyzed cyclization of N-aryl-fluorinated imidoyl iodides with terminal alkynes. The reaction proceeds in modest to excellent yields and tolerates ortho-, meta- and para-substitution on the aryl component, although meta-substitution leads to a mixture of products. The presence of the α-H on the terminal alkyne was found to be integral for the success of this reaction. When non-fluorinated alkynylimines were used as starting materials, pyrrole products were formed. This is possibly due to the strong electron-withdrawing effect of the fluorines, whereby the electron density and nucleophilicity of nitrogen is greatly reduced. Based on above discoveries, a mechanism involving allene intermediates was proposed.