Palladium-Catalyzed Asymmetric Allylic Fluoroalkylation/Trifluoromethylation

The first palladium-catalyzed asymmetric allylic trifluoromethylation is disclosed. The methodology evokes a fundamental principle by which the synergistic interplay of a leaving group and its subsequent activation of the nucleophilic trifluoromethyl group enabled the reaction. Allyl fluorides have...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 141; no. 29; pp. 11446 - 11451
Main Authors Trost, Barry M, Gholami, Hadi, Zell, Daniel
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.07.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
REAGENT
KETONES
SUBSTITUTION
DESIGN
CARBON
FLUORINE
TRIFLUOROMETHYLATION
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Summary:The first palladium-catalyzed asymmetric allylic trifluoromethylation is disclosed. The methodology evokes a fundamental principle by which the synergistic interplay of a leaving group and its subsequent activation of the nucleophilic trifluoromethyl group enabled the reaction. Allyl fluorides have been shown to be superior precursors for generation of π-allyl complexes, which lead to trifluoromethylated products with high selectivities and functional group tolerance. This study highlights the unique role of a bidentate diamidophosphite ligand class in palladium-catalyzed reactions that allow a challenging transformation to proceed.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b06231