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Selectfluor-Mediated Simultaneous Cleavage of C-O and C-C Bonds in α,β-Epoxy Ketones Under Transition-Metal-Free Conditions: A Route to 1,2-Diketones

Heng Wang, Shaobo Ren, Jian Zhang, Wei Zhang and Yunkui Liu*

*State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China, Email: ykuiliuzjut.edu.cn

H. Wang, S. Ren, J. Zhang, W. Zhang, Y. Liu, J. Org. Chem., 2015, 80, 6856-6863.

DOI: 10.1021/acs.joc.5b00857 (free Supporting Information)


 

Abstract

A Selectfluor-mediated reaction of α,β-epoxy ketones provides 1,2-diketones in good yields under transition-metal-free oxidative conditions via a ring-opening/benzoyl rearrangement/C-C bond cleavage sequence.

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A Combination of Copper(0) Powder and Selectfluor Enables Generation of Cationic Copper Species for Mild 1,2-Dicarbonylation of Alkynes

W. Zhang, J. Zhang, Y. Liu, Z. Xu, Synlett, 2013, 24, 2709-2714.


Key Words

1,2-diketones, Selectfluor


ID: J42-Y2015