This work was supported by NSERC (Canada) and The Ontario Research Fund (ORF) (Ontario).
Higher-Order Zincates as Transmetalators in Alkyl–Alkyl Negishi Cross-Coupling†
Article first published online: 8 JUN 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 28, pages 7024–7027, July 9, 2012
How to Cite
McCann, L. C., Hunter, H. N., Clyburne, J. A. C. and Organ, M. G. (2012), Higher-Order Zincates as Transmetalators in Alkyl–Alkyl Negishi Cross-Coupling . Angew. Chem. Int. Ed., 51: 7024–7027. doi: 10.1002/anie.201203547
- Issue published online: 4 JUL 2012
- Article first published online: 8 JUN 2012
- Manuscript Received: 8 MAY 2012
- NSERC (Canada)
- The Ontario Research Fund (ORF) (Ontario)
- Negishi reaction;
Negishi revisited: Higher-order alkyl zincates have been subjected to Negishi coupling with alkyl bromides. For the first time, coupling takes place in straight THF, i.e., without a salt additive and a high dielectric co-solvent. This provides evidence that it is the higher-order zincate that undergoes transmetalation to Pd, and not mono-anionic zincates or any of the other species present in the Schlenk equilibrium.