Decarboxylative aldol reaction of α,α-difluoro-β-ketocarboxylate salt: a facile method for generation of difluoroenolate

We developed a decarboxylative aldol reaction using α,α-difluoro-β-ketocarboxylate salt, carbonyl compounds, and ZnCl / , , ', '-tetramethylethylenediamine. The generation of difluoroenolate proceeded smoothly under mild heating to provide α,α-difluoro-β-hydroxy ketones in good to excellen...

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Published inRSC advances Vol. 8; no. 37; pp. 20568 - 20575
Main Authors Tarui, Atsushi, Oduti, Mayuna, Shinya, Susumu, Sato, Kazuyuki, Omote, Masaaki
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 05.06.2018
The Royal Society of Chemistry
Subjects
Aldehydes
Carbonyl compounds
Carbonyls
Chemistry
Ketones
Zinc chloride
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Summary:We developed a decarboxylative aldol reaction using α,α-difluoro-β-ketocarboxylate salt, carbonyl compounds, and ZnCl / , , ', '-tetramethylethylenediamine. The generation of difluoroenolate proceeded smoothly under mild heating to provide α,α-difluoro-β-hydroxy ketones in good to excellent yield (up to 99%). The α,α-difluoro-β-ketocarboxylate salt was bench stable and easy to handle under air, which realizes a convenient and environmentally friendly methodology for synthesis of difluoromethylene compounds.
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ISSN:2046-2069
2046-2069
DOI:10.1039/c8ra02440e