Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 29, Pages 11446-11451Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b06231
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Funding
- Tamaki Foundation
- Chugai Pharmaceuticals
- DFG Research Fellowship
- National Science Foundation [ECCS-1542152]
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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 pi-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.
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