Domino-Fluorination–Protodefluorination Enables Decarboxylative Cross-Coupling of α‑Oxocarboxylic Acids with Styrene via Photoredox Catalysis
Domino-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...
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Veröffentlicht in: | Journal of organic chemistry 2017-09, Vol.82 (18), p.9305-9311 |
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Hauptverfasser: | , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | Domino-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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.7b01054 |