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Dichlorination of α-Diazo-β-dicarbonyls Using (Dichloroiodo)benzene

Keith E. Coffey, Graham K. Murphy*

*Department of Chemistry, University of Waterloo, 200 University Ave W., Waterloo, ON, N2L 3G1, Canada, Email: graham.murphyuwaterloo.ca

K. E. Coffrey, G. K. Murphy, Synlett, 2015, 26, 1003-1007.

DOI: 10.1055/s-0034-1380304 (free Supporting Information)


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Abstract

α-Diazo-β-dicarbonyl compounds were chlorinated using (dichloro)iodobenzene and an activating catalyst. Acyclic diazocarbonyls reacted faster than cyclics, and β-diketones were much faster to react than β-keto esters or β-diesters.

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Dihaloiodoarenes: α,α-Dihalogenation of Phenylacetate Derivatives

J. Tao, R. Tran, G. K. Murphy, J. Am. Chem. Soc., 2013, 135, 16312-16315.


Key Words

diazo compounds, iodobenzene dichloride, α-chloroketones, α-chlorocarboxylic esters, catalysis, ylides


ID: J60-Y2015