by Jason Tao, Richard Tran and Graham K. Murphy*
A hypervalent iodine reagent-based α-carbonyl
dihalogenation reaction is reported. Treating 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 activation of the aryl-λ3-iodane
(ArIX2) species and proceeds rapidly and chemoselectively to the
desired gem-difunctionalized products in good to excellent yield.
Journal of the American Chemical Society
Publication Date (Web): October 23, 2013
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