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Bimolecular vinylation of arenes by vinyl cations

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Abstract

Styrene derivatives can be easily synthesized from vinyl triflates and arenes under mild reaction conditions, using [Li][Al(OC(CF3)3)4] as a catalyst and LiHMDS as a base. This transformation is likely to involve a vinyl cation intermediate as an electrophile, which is corroborated by DFT calculations, deuterium-labeling and other control experiments. The use of an inert weakly coordinating anion is a decisive factor in this bimolecular vinylation process.

Graphical abstract: Bimolecular vinylation of arenes by vinyl cations

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Article information


Submitted
30 Mar 2020
Accepted
05 May 2020
First published
05 May 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Bimolecular vinylation of arenes by vinyl cations

Z. Li, V. Gandon and C. Bour, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC02300K

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