Rapid Injection NMR in Mechanistic Organocopper Chemistry, part 4. For part 3, see reference [9]. NSF grants 0353061 and 0321056 supported this work. The authors thank D. Deadwyler for the fabrication and maintenance of the rapid-injection equipment, JEOL for their technical assistance, and J.P. Snyder for many helpful discussions.
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Communication
Organocuprate Cross-Coupling: The Central Role of the Copper(III) Intermediate and the Importance of the Copper(I) Precursor†
Article first published online: 22 AUG 2007
DOI: 10.1002/anie.200703035
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 46, Issue 37, pages 7082–7085, September 17, 2007
Additional Information
How to Cite
Bertz, Steven H., Cope, S., Dorton, D., Murphy, M. and Ogle, Craig A. (2007), Organocuprate Cross-Coupling: The Central Role of the Copper(III) Intermediate and the Importance of the Copper(I) Precursor. Angew. Chem. Int. Ed., 46: 7082–7085. doi: 10.1002/anie.200703035
- †
Publication History
- Issue published online: 11 SEP 2007
- Article first published online: 22 AUG 2007
- Manuscript Received: 8 JUL 2007
Funded by
- NSF. Grant Numbers: 0353061, 0321056
Keywords:
- copper;
- cross-coupling;
- isotopic labeling;
- NMR spectroscopy;
- S ligands
CuIIIin focus: The key intermediate in copper-mediated cross-coupling reactions has long been believed to be a “copper(III) intermediate”. Investigation of reactions of a variety of methyl Gilman reagents Me2CuLi⋅LiX with EtI using rapid-injection NMR spectroscopy conditions reveals a number of formally CuIII tetracoordinate square-planar intermediates (see scheme) with a surprising range of stabilities.