Synthesis 2016; 48(15): 2376-2384
DOI: 10.1055/s-0035-1561433
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© Georg Thieme Verlag Stuttgart · New York

Detrifluoroacetylative Generation of Halogenated Enolates: Practical Access to Perhalogenated Ketones and Alkenes

Kaluvu Balaraman
Georgetown University, Chemistry Department, Washington, DC, USA   Email: cw27@georgetown.edu
,
Max Moskowitz
Georgetown University, Chemistry Department, Washington, DC, USA   Email: cw27@georgetown.edu
,
Yang Liu
Georgetown University, Chemistry Department, Washington, DC, USA   Email: cw27@georgetown.edu
,
Christian Wolf*
Georgetown University, Chemistry Department, Washington, DC, USA   Email: cw27@georgetown.edu
› Author Affiliations
Further Information

Publication History

Received: 29.02 2016

Accepted after revision: 11 March 2016

Publication Date:
20 April 2016 (online)


Abstract

Sequential chlorination/fluorination of aromatic trifluoroacetylated ketones gives 1-aryl 2-chloro-2,4,4,4-tetrafluorobutan-1,3-dione hydrates that are used for the synthesis of ketones and alkenes exhibiting a terminal bromochlorofluoromethyl group. The hydrates undergo detrifluoroacetylative cleavage and subsequent bromination in the presence of a copper(II) bisoxazoline catalyst, K2CO3, and NBS at room temperature. The corresponding bromochlorofluoromethyl ketones can be applied in Wittig and Horner–Wadsworth–Emmons reactions and dibromoalkenylations.

Supporting Information

 
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