Metal-free carbon–carbon cross-couplings between the ion pairs in sulfonium tetraphenylborates

A series of sulfonium tetraphenylborates can be readily prepared by the metathesis of sulfonium halides with sodium tetraphenylborates. After heating at 120–150°C, the sulfonium tetraphenylborates can smoothly undergo the cross-couplings between the tetraphenylborate anions and the sulfonium cations...

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Bibliographic Details
Published in:Tetrahedron letters 2014-07, Vol.55 (30), p.4230-4232
Main Authors: Xu, Mei-Li, Huang, Wenhua
Format: Article
Language:English
Subjects:
Carbon-carbon composites
Carbonyls
Carbon–carbon bond formation
Chemical reactions
Cross coupling
Heating
Ion pairs
Metal-free
Phenylation
Sodium
Sulfonium tetraphenylborate
Tetrahedrons
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Summary:A series of sulfonium tetraphenylborates can be readily prepared by the metathesis of sulfonium halides with sodium tetraphenylborates. After heating at 120–150°C, the sulfonium tetraphenylborates can smoothly undergo the cross-couplings between the tetraphenylborate anions and the sulfonium cations in the absence of a metal catalyst. For carbonylmethyl-, benzyl-, and allylsulfoniums, the corresponding carbonylmethyl–phenyl, benzyl–phenyl, and allyl–phenyl cross-coupling products can be obtained in 22–76% yields. An interionic electron-transfer mechanism for this cross-coupling reaction is proposed.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.05.102