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...

Full description

Saved in:
Bibliographic Details
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
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201202219