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Domino-Fluorination–Protodefluorination Enables Decarboxylative Cross-Coupling of α‑Oxocarboxylic Acids with Styrene via Photoredox Catalysis

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posted on 2017-08-15, 00:00 authored by Muliang Zhang, Junwei Xi, Rehanguli Ruzi, Nan Li, Zhongkai Wu, Weipeng Li, Chengjian Zhu
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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