jo7b01054_si_001.pdf (1.02 MB)
Domino-Fluorination–Protodefluorination Enables Decarboxylative Cross-Coupling of α‑Oxocarboxylic Acids with Styrene via Photoredox Catalysis
journal contribution
posted on 2017-08-15, 00:00 authored by Muliang Zhang, Junwei Xi, Rehanguli Ruzi, Nan Li, Zhongkai Wu, Weipeng Li, Chengjian ZhuDomino-fluorination–protodefluorination
decarboxylative
cross-coupling of α-keto acids with styrene has been developed
via photoredox catalysis. The critical part of this strategy is the
formation of the carbon–fluorine (C–F) bond by the capture
of a carbon-centered radical intermediate, which will overcome side
reactions during the styrene radical functionalization process. Experimental
studies have provided evidence indicating a domino-fluorination–protodefluorination
pathway with α-keto acid initiating the photoredox cycle. The
present catalytic protocol also affords a novel approach for the construction
of α,β-unsaturated ketones under mild conditions.
History
Usage metrics
Categories
Keywords
PhotoredoxStyrenecross-couplingevidenceα- keto acidDomino-fluorinationnovel approachExperimental studiesDecarboxylativephotoredox catalysisEnableCatalysistyreneα- keto acidsstrategyDomino-Fluorinationdecarboxylativeconstructioncarbon-centeredside reactionsCross-Couplingdomino-fluorinationformationphotoredox cycleOxocarboxylicketonefunctionalization processpathwayAcidbond
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC