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Copper-mediated cascade radical cyclization of olefins with naphthalenyl iododifluoromethyl ketones

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Abstract

Copper-mediated radical cyclization of naphthalenyl iododifluoromethyl ketones with olefins was successfully developed to generate a series of unprecedented gem-difluorodihydrophenanthrenones, especially 2,2-difluoro-3,4-dihydrophenanthren-1(2H)-one derivatives. This strategy features the use of cheap copper powder and excellent regioselectivity and diastereoselectivity, thus providing a facile approach for application in drug discovery and development. Preliminary mechanistic studies indicate the involvement of difluorinated radical intermediates. Density functional theory (DFT) calculation was performed to provide further evidence for regioselectivity.

Graphical abstract: Copper-mediated cascade radical cyclization of olefins with naphthalenyl iododifluoromethyl ketones

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Publication details

The article was received on 21 Apr 2019, accepted on 11 Jun 2019 and first published on 12 Jun 2019


Article type: Paper
DOI: 10.1039/C9OB00916G
Org. Biomol. Chem., 2019, Advance Article

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    Copper-mediated cascade radical cyclization of olefins with naphthalenyl iododifluoromethyl ketones

    P. Peng, G. Huang, Y. Sun, X. Wang, J. Wu and F. Wu, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00916G

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