Issue 44, 2018

Cyclopropanation of alkenes with metallocarbenes generated from monocarbonyl iodonium ylides

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

Supplementary files

Article information

Article type
Communication
Submitted
10 Okt 2018
Accepted
25 Okt 2018
First published
25 Okt 2018

Org. Biomol. Chem., 2018,16, 8486-8490

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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