This research was supported by a grant (CHE-0450638) from the National Science Foundation. J.P.C and A.B.L. thank Amgen for financial support. M.T.G thanks the Deutscher Akademischer Austauschdienst for financial support. We thank Allen Oliver at the University of California, Santa Cruz and Prateek Verma at Stanford University for X-ray crystal structures. We also thank Kristen Brownell for assisting in substrate preparation.
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Communication
The Synthesis of Highly Substituted Cyclooctatetraene Scaffolds by Metal-Catalyzed [2+2+2+2] Cycloadditions: Studies on Regioselectivity, Dynamic Properties, and Metal Chelation†
Article first published online: 8 SEP 2009
DOI: 10.1002/anie.200903859
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 48, Issue 41, pages 7687–7690, September 28, 2009
Additional Information
How to Cite
Wender, Paul A., Christy, Justin P., Lesser, Adam B. and Gieseler, Marc T. (2009), The Synthesis of Highly Substituted Cyclooctatetraene Scaffolds by Metal-Catalyzed [2+2+2+2] Cycloadditions: Studies on Regioselectivity, Dynamic Properties, and Metal Chelation. Angew. Chem. Int. Ed., 48: 7687–7690. doi: 10.1002/anie.200903859
- †
Publication History
- Issue published online: 23 SEP 2009
- Article first published online: 8 SEP 2009
- Manuscript Received: 14 JUL 2009
Funded by
- National Science Foundation
- Amgen
- Deutscher Akademischer Austauschdienst
Keywords:
- cycloadditions;
- cyclooctatetraenes;
- diynes;
- homogeneous catalysis;
- oxazoline ligands
All-kynes of COTs: A Ni0-catalyzed [2+2+2+2] cycloaddition of 1,6-diynes yields highly functionalized hexa- and octa-substituted cyclooctatetraenes (COTs; see picture) along with the first example of a fully intramolecular [2+2+2+2] cycloaddition product. The regioselectivity of this process is studied and the initial use of COT ligands is shown in the formation of a ZnII complex with a bis(oxazoline) COT.