Regioselective polyfluoroarylation of alkenyl C–H bonds via aryl to vinyl 1,4-palladium migration

Efficient palladium-catalyzed regioselective vinylic C–H polyfluoroarylation of gem-disubstituted ethylenes with polyfluoroarenes was realized to access a variety of polyfluorinated triarylethenes. An aryl to vinyl 1,4-palladium migration is proposed to achieve high regio- and stereoselectivities fo...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2023-10, Vol.10 (20), p.5144-5150
Main Authors: Lin, Jie, Ma, Juan, Wang, Liandi, Wu, Kaikai, Yong-Gui, Zhou, Yu, Zhengkun
Format: Article
Language:English
Subjects:
Aromatic compounds
Functional groups
Intermediates
Organic chemistry
Palladium
Protonation
Regioselectivity
Substrates
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Summary:Efficient palladium-catalyzed regioselective vinylic C–H polyfluoroarylation of gem-disubstituted ethylenes with polyfluoroarenes was realized to access a variety of polyfluorinated triarylethenes. An aryl to vinyl 1,4-palladium migration is proposed to achieve high regio- and stereoselectivities for the target products. This strategy features broad substrate scopes and good functional group tolerance. Mechanistic studies have suggested that a protonation–deprotonation process reversibly occurs between a five-membered palladacycle and the vinyl–palladium intermediates, and aromatic C–H cleavage of polyfluoroarenes contributes to the rate-limiting step in the overall catalytic cycle.
ISSN:2052-4110
2052-4110
DOI:10.1039/d3qo01099f