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
Hauptverfasser: Zhang, Muliang, Xi, Junwei, Ruzi, Rehanguli, Li, Nan, Wu, Zhongkai, Li, Weipeng, Zhu, Chengjian
Format: Artikel
Sprache:eng
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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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b01054