Unknown

Dataset Information

0

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


ABSTRACT: Sequential chlorination/fluorination of aromatic trifluoroacetylated ketones gives 1-aryl 2-chloro-2,4,4,4-tetrafluoro-butan-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.

SUBMITTER: Balaraman K 

PROVIDER: S-EPMC5589145 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

altmetric image

Publications

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

Balaraman Kaluvu K   Moskowitz Max M   Liu Yang Y   Wolf Christian C  

Synthesis 20160420 15


Sequential chlorination/fluorination of aromatic trifluoroacetylated ketones gives 1-aryl 2-chloro-2,4,4,4-tetrafluoro-butan-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, K<sub>2</sub>CO<sub>3</sub> and NBS at room temperature. The corresponding bromochlorofluoromethyl ketones can be  ...[more]

Similar Datasets

| S-EPMC4159307 | biostudies-literature
| S-EPMC2636850 | biostudies-literature
| S-EPMC6823458 | biostudies-literature
| S-EPMC4195513 | biostudies-literature
| S-EPMC6604859 | biostudies-literature
| S-EPMC4192553 | biostudies-literature
| S-EPMC5628582 | biostudies-literature
| S-EPMC2936481 | biostudies-literature
| S-EPMC6534616 | biostudies-literature
| S-EPMC9704012 | biostudies-literature