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Copper-Catalyzed Regioselective Reaction of Internal Alkynes and Diaryliodonium Salts

Ze-Feng Xu, Chen-Xin Cai and Jin-Tao Liu*

*Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032, China, Email: jtliusioc.ac.cn

Z.-F. Xu, C.-X. Cai, J.-T. Liu, Org. Lett., 2013, 15, 2096-2099.

DOI: 10.1021/ol4003543 (free Supporting Information)



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Abstract

The copper-catalyzed highly regioselective reaction of aryl alkyl alkynes and arylpropargylic alcohols with diaryliodonium salts gives α-arylketones in good yields under mild conditions. Depending on the internal alkyne substrate,  two different arylation-oxygenation pathways under different reaction conditions have been elaborated based on deuterated experiments, controlling experiments, and spectroscopic analysis of reaction intermediates.

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Key Words

α-Arylketones, Oxygen


ID: J54-Y2013