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Issue 13, 2019
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Radical-induced ring-opening and reconstruction of cyclobutanone oxime esters

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Abstract

The first example of intramolecular ring-opening and reconstruction of cyclobutanone oxime esters via selective C–C bond cleavage leading to the synthesis of 3,4-dihydronaphthalene-2-carbonitriles in the presence of a cheap copper catalyst has been reported. The protocol is distinguished by mild and safe reaction conditions that exclude ligands, oxidants, bases, toxic cyanide salts and tolerates a wide scope of cyclobutanones without compromising their efficiency and scalability. The alternative visible-light-driven photoredox process for this coupling reaction was also uncovered.

Graphical abstract: Radical-induced ring-opening and reconstruction of cyclobutanone oxime esters

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Publication details

The article was received on 21 Dec 2018, accepted on 14 Jan 2019 and first published on 14 Jan 2019


Article type: Communication
DOI: 10.1039/C8CC10109D
Chem. Commun., 2019,55, 1971-1974

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    Radical-induced ring-opening and reconstruction of cyclobutanone oxime esters

    P. Wang, B. Zhao, Y. Yuan and Z. Shi, Chem. Commun., 2019, 55, 1971
    DOI: 10.1039/C8CC10109D

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