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. 2012 Jan 27;51(5):1225-7.
doi: 10.1002/anie.201106969. Epub 2011 Dec 15.

One-pot arylative epoxidation of ketones by employing amphoteric bromoperfluoroarenes

Zhou Li  1 , Vladimir Gevorgyan
Affiliations

One-pot arylative epoxidation of ketones by employing amphoteric bromoperfluoroarenes

Zhou Li et al. Angew Chem Int Ed Engl. .

Abstract

A one-pot cascade arylative epoxidation of enolizable ketones with bromopentafluorobenzene (PFPBr) and derivatives into perfluoroaryl oxiranes is reported. PFPBr is utilized as an equivalent of Br+ and PFP− in this highly efficient, easily scaled up and diastereoselective epoxidation reaction, which produces synthetically useful polyfluoroaryl oxiranes.

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Figures

Scheme 1
Scheme 1
Diverse Reactivity of PFPBr.
Scheme 2
Scheme 2
Proposed Reaction Path for Epoxidation of Ketones with PFPBr.
Scheme 3
Scheme 3
Semipinacol Rearrangement of Oxiranes.
Scheme 4
Scheme 4
SNAr on Pentafluorophenyl Ring.
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