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Updated: Jun 27, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
General method for the synthesis of phenyliodonium ylides from malonate esters: easy access to 1,1-cyclopropane
Sébastien R Goudreau1, David Marcoux, André B Charette
1Departement de chimie, Universite de Montreal, P.O. Box 6128, Station Downtown, Montreal, Quebec, Canada H3C 3J7.
Abstract:
A general method to access phenyliodonium ylides from malonates has been developed. These ylides provide easy access to a variety of useful 1,1-cyclopropane diesters using rhodium or copper catalysis. Moreover, the iodonium ylide of dimethyl malonate was obtained in 78% yield using improved conditions that involve a simple filtration step to isolate the desired product. This ylide was shown to be a safer and convenient alternative to the corresponding diazo compound and a very efficient way to 1,1-cyclopropane diesters when used with a catalytic amount of Rh(2)(esp)(2).
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