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Dihaloiodoarenes: α,α-Dihalogenation of Phenylacetate Derivatives

Jason Tao, Richard Tran and Graham K. Murphy*

*Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada, N2L3G1, Email: graham.murphyuwaterloo.ca

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

DOI: 10.1021/ja408678p (free Supporting Information)


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Abstract

A hypervalent iodine reagent-based α-carbonyl dihalogenation of diazoacetate derivatives with either iodobenzene dichloride or iodotoluene difluoride results in gem-dichlorination or gem-difluorination products, respectively. The reaction is catalyzed by either Lewis acid or Lewis base and proceeds rapidly and chemoselectively to the desired gem-difunctionalized products in very good yield.

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

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


Key Words

α-chlorination, benzyl chlorides, iodobenzene dichloride


ID: J48-Y2013