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

5 years ago

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

Weipeng Li, Zhongkai Wu, Nan Li, Rehanguli Ruzi, Muliang Zhang, Chengjian Zhu, Junwei Xi

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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01054

DOI: 10.1021/acs.joc.7b01054