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Issue 44, 2018
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Cyclopropanation of alkenes with metallocarbenes generated from monocarbonyl iodonium ylides

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Abstract

Reacting Wittig reagents and the hypervalent iodine reagent iodosotoluene, in the presence of 10 mol% Cu(tfacac)2 and 5 equiv. of alkene, results in a novel cyclopropanation reaction. The reagent combination is believed to generate a transient monocarbonyl iodonium ylide (MCIY) in situ, which can be intercepted by the copper catalyst to give a metallocarbene. Both ester and ketone derived phosphoranes can be used, as can styrenyl and non-styrenyl alkenes, which provides cyclopropanes in yields up to 81%.

Graphical abstract: Cyclopropanation of alkenes with metallocarbenes generated from monocarbonyl iodonium ylides

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Publication details

The article was received on 10 Oct 2018, accepted on 25 Oct 2018 and first published on 25 Oct 2018


Article type: Communication
DOI: 10.1039/C8OB02636J
Citation: Org. Biomol. Chem., 2018,16, 8486-8490
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    Cyclopropanation of alkenes with metallocarbenes generated from monocarbonyl iodonium ylides

    T. Chidley and G. K. Murphy, Org. Biomol. Chem., 2018, 16, 8486
    DOI: 10.1039/C8OB02636J

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