We thank the National Science Foundation (grant: CHE-0309613), the National Institutes of Health (grant: GM 36792), and Purdue University for support of this research.
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Communication
Highly Stereoselective Synthesis of (1E)-2-Methyl-1,3-dienes by Palladium-Catalyzed trans-Selective Cross-Coupling of 1,1-Dibromo-1-alkenes with Alkenylzinc Reagents†
Article first published online: 16 APR 2004
DOI: 10.1002/anie.200353022
Copyright © 2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Zeng, X., Qian, M., Hu, Q. and Negishi, E.-i. (2004), Highly Stereoselective Synthesis of (1E)-2-Methyl-1,3-dienes by Palladium-Catalyzed trans-Selective Cross-Coupling of 1,1-Dibromo-1-alkenes with Alkenylzinc Reagents. Angewandte Chemie International Edition, 43: 2259–2263. doi: 10.1002/anie.200353022
- †
Publication History
- Issue published online: 16 APR 2004
- Article first published online: 16 APR 2004
- Manuscript Revised: 12 FEB 2004
- Manuscript Received: 7 OCT 2003
Keywords:
- carbene ligands;
- cross-coupling;
- dienes;
- methylation;
- palladium
Graphical Abstract
Ligand control: The use of Pd complexes containing tBu3P or nitrogen-heterocyclic carbene (NHC) ligands almost completely prevents stereoisomerization, thereby permitting an efficient and selective methylation and higher alkylation of (Z)-2-bromo-1,3-dienes (see scheme, dba=trans,trans-dibenzylideneacetone).