Chemoselective α-Methylenation of Aromatic Ketones Using the NaAuCl₄/Selectfluor/DMSO System

Hongbo Zhu, Xin Meng, Yanhui Zhang, Guang Chen, Ziping Cao*, Xuejun Sun and Jinmao You*

*School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165, China, Email: caozp_qfnu163.com, jmyou6304163.com

H. Zhu, X. Meng, Y. Zhang, G. Chen, Z. Cao, X. Sun, J. You, J. Org. Chem., 2017, 82, 12059-12065.

DOI: 10.1021/acs.joc.7b01790

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Abstract

Gold catalysis enables a chemoselective α-methylenation of aromatic ketones using Selectfluor as a methylenating agent to provide various 1,2-disubstituted propenone derivatives in good yields. This reaction offers simple operation, good functional group tolerance, and broad scope of substrates.

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proposed mechanism

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Key Words

enones, methylenation, Selectfluor

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ID: J42-Y2017