We thank the Fonds der Chemischen Industrie and the European Research Council (ERC) for financial support. We also thank BASF SE (Ludwigshafen) and Chemetall GmbH (Frankfurt) for the generous gift of chemicals.
Improved Air-Stable Solid Aromatic and Heterocyclic Zinc Reagents by Highly Selective Metalations for Negishi Cross-Couplings†
Article first published online: 21 AUG 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 37, pages 9428–9432, September 10, 2012
How to Cite
Stathakis, C. I., Bernhardt, S., Quint, V. and Knochel, P. (2012), Improved Air-Stable Solid Aromatic and Heterocyclic Zinc Reagents by Highly Selective Metalations for Negishi Cross-Couplings . Angew. Chem. Int. Ed., 51: 9428–9432. doi: 10.1002/anie.201204526
- Issue published online: 5 SEP 2012
- Article first published online: 21 AUG 2012
- Manuscript Received: 11 JUN 2012
- Fonds der Chemischen Industrie
- European Research Council (ERC)
- organozinc reagents;
Directed metalation using TMPMgCl⋅LiCl (TMP=2,2,6,6-tetramethylpiperidide) and subsequent transmetalation with Zn(OPiv)2 leads to aryl and heteroaryl zinc pivalates. After solvent evaporation, easy-to-handle fine powders are obtained that retain most of their activity (>85 %) when exposed to air for 4 h. They smoothly undergo Negishi cross-couplings, and technical-grade solvents can be used without significant loss of yield.