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Vinyl cations exhibit remarkable reactivity towards arene C–H functionalizations. This computational study revealed the key mechanistic details of intramolecular C–H vinylation through a vinyl cation intermediate. Based on the reaction mechanism, the effects of substitution, ring strain and tether length on the reactivity of the vinyl cation were elucidated.

Graphical abstract: Divergent pathway and reactivity control of intramolecular arene C–H vinylation by vinyl cations

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