One-pot arylative epoxidation of ketones by employing amphoteric bromoperfluoroarenes

Zhou Li; Vladimir Gevorgyan

doi:10.1002/anie.201106969

One-pot arylative epoxidation of ketones by employing amphoteric bromoperfluoroarenes

Zhou Li, Vladimir Gevorgyan

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

A one-pot cascade synthesis of perfluoroaryl oxiranes 2 by the arylative epoxidation of enolizable ketones 1 with bromopentafluorobenzene (PFPBr) and derivatives (3) is reported. PFPBr is utilized as an equivalent of Br ⁺ and PFP ^- in this highly efficient, easily scaled-up, diastereoselective epoxidation reaction, which produces synthetically useful polyfluoroaryl oxiranes.

Original language	English (US)
Pages (from-to)	1225-1227
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	5
DOIs	https://doi.org/10.1002/anie.201106969
State	Published - Jan 27 2012
Externally published	Yes

Keywords

bromopentafluorobenzene
cascade transformations
epoxidation
perfluorinated compounds
perfluoroarylepoxides

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201106969

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abstract = "A one-pot cascade synthesis of perfluoroaryl oxiranes 2 by the arylative epoxidation of enolizable ketones 1 with bromopentafluorobenzene (PFPBr) and derivatives (3) is reported. PFPBr is utilized as an equivalent of Br + and PFP - in this highly efficient, easily scaled-up, diastereoselective epoxidation reaction, which produces synthetically useful polyfluoroaryl oxiranes.",

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author = "Zhou Li and Vladimir Gevorgyan",

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AU - Li, Zhou

AU - Gevorgyan, Vladimir

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N2 - A one-pot cascade synthesis of perfluoroaryl oxiranes 2 by the arylative epoxidation of enolizable ketones 1 with bromopentafluorobenzene (PFPBr) and derivatives (3) is reported. PFPBr is utilized as an equivalent of Br + and PFP - in this highly efficient, easily scaled-up, diastereoselective epoxidation reaction, which produces synthetically useful polyfluoroaryl oxiranes.

AB - A one-pot cascade synthesis of perfluoroaryl oxiranes 2 by the arylative epoxidation of enolizable ketones 1 with bromopentafluorobenzene (PFPBr) and derivatives (3) is reported. PFPBr is utilized as an equivalent of Br + and PFP - in this highly efficient, easily scaled-up, diastereoselective epoxidation reaction, which produces synthetically useful polyfluoroaryl oxiranes.

KW - bromopentafluorobenzene

KW - cascade transformations

KW - epoxidation

KW - perfluorinated compounds

KW - perfluoroarylepoxides

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 5

ER -

One-pot arylative epoxidation of ketones by employing amphoteric bromoperfluoroarenes

Abstract

Keywords

ASJC Scopus subject areas

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