Exploiting Boron-Zinc Transmetallation for the Arylation of Benzyl Halides: What are the Reactive Species?

One step Beyond: The transmetallation reactions of ArB(OH)2 and Ar3B3O3 with Et2Zn are far more complicated than previously supposed, with solvent‐dependent equilibria between ArB(OY)2 at one side and [RZn(solv)3][BR4] at the other (see picture). While the role of the highly reactive organozinc cati...

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Published in:Angewandte Chemie International Edition 2012-05, Vol.51 (22), p.5435-5438
Main Authors: Bedford, Robin B., Gower, Nicholas J., Haddow, Mairi F., Harvey, Jeremy N., Nunn, Joshua, Okopie, Rukeme A., Sankey, Rosalind F.
Format: Article
Language:English
Subjects:
Activation
arylation
benzyl halides
boron
Cations
Halides
Pictures
transmetallation
zinc
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description One step Beyond: The transmetallation reactions of ArB(OH)2 and Ar3B3O3 with Et2Zn are far more complicated than previously supposed, with solvent‐dependent equilibria between ArB(OY)2 at one side and [RZn(solv)3][BR4] at the other (see picture). While the role of the highly reactive organozinc cation has not been implicated before, its importance for the activation of an otherwise sluggish class of electrophiles is shown.
doi_str_mv 10.1002/anie.201202219
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subjects Activation
arylation
benzyl halides
boron
Cations
Halides
Pictures
transmetallation
zinc
title Exploiting Boron-Zinc Transmetallation for the Arylation of Benzyl Halides: What are the Reactive Species?
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