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Issue 16, 2019
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Visible-light-induced consecutive C–C bond fragmentation and formation for the synthesis of elusive unsymmetric 1,8-dicarbonyl compounds

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Abstract

Synthesis of the valuable unsymmetric 1,8-dicarbonyl compounds remains underexplored currently. Herein, we disclose a new strategy for the synthesis of 1,8-diketones through the coupling of cyclopropanols and cyanohydrins under visible-light irradiation. The protocol features a cascade of intriguing ring opening of cyclopropanols and remote cyano migration. The unfavorable addition of an alkyl radical to an electron-rich alkene is facilitated by the intramolecular cyanohydrin interception. A variety of multiply functionalized 1,8-diketones are furnished in useful yields. The products could be further transformed into other valuable compounds, manifesting the utility of this method.

Graphical abstract: Visible-light-induced consecutive C–C bond fragmentation and formation for the synthesis of elusive unsymmetric 1,8-dicarbonyl compounds

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Publication details

The article was received on 16 Jan 2019, accepted on 30 Jan 2019 and first published on 30 Jan 2019


Article type: Communication
DOI: 10.1039/C9CC00378A
Citation: Chem. Commun., 2019,55, 2368-2371

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    Visible-light-induced consecutive C–C bond fragmentation and formation for the synthesis of elusive unsymmetric 1,8-dicarbonyl compounds

    M. Ji, Z. Wu and C. Zhu, Chem. Commun., 2019, 55, 2368
    DOI: 10.1039/C9CC00378A

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