Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 43, Pages 18698-18705Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c09505
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Funding
- NSF [CHE-0840456, CHE 1955284]
- Rackham Graduate Student Research Grant (MMWW)
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When subjected to arylboranes, anionic trifluoromethyl and difluorobenzyl palladium(II) complexes undergo fluoride abstraction followed by 1,1-migratory insertion. The resulting intermediate fluoroalkyl species can be induced to undergo a subsequent transmetalation and reductive elimination from either an in situ formed fluoroboronate (FB(Ar-3)(-)) or an exogenous boronic acid/ ester (ArB(OR)(2)) and nucleophilic activator, representing a net defluorinative arylation reaction. The latter method enabled a structurally diverse substrate scope to be prepared from either an isolated palladium-CF3 complex, or from Pd(PPh3)(4) and other commercially available reagents.
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