Published November 5, 2009
| Version Accepted Version + Supplemental Material
Journal Article
Open
On the Impact of Steric and Electronic Properties of Ligands on Gold(I)-Catalyzed Cycloaddition Reactions
Creators
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1.
California Institute of Technology
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2.
University of California System
Abstract
It is shown that [4 + 3] and [4 + 2] cycloaddition pathways are accessible in the Au(I) catalysis of allene−dienes. Seven-membered ring gold-stabilized carbenes, originating from the [4 + 3] cycloaddition process, are unstable and can rearrange via a 1,2-H or a 1,2-alkyl shift to yield six- and seven-membered products. Both steric and electronic properties of the AuL^+ catalyst affect the electronic structure of the intermediate gold-stabilized carbene and its subsequent reactivity.
Additional Information
© 2009 American Chemical Society. Received August 4, 2009. Publication Date (Web): September 25, 2009. We gratefully acknowledge NIHGMS (RO1 GM073932), Bristol-Myers Squibb, and Novartis for funding and Johnson Matthey for the generous donation of AuCl_3. Facilities were funded by grants from ARO-DURIP and ONR-DURIP. Supporting Information Available: Supplied are XYZ coordinates. This material is available free of charge via the Internet at http://pubs.acs.org.Attached Files
Accepted Version - nihms149287.pdf
Supplemental Material - ol9018002_si_001.pdf
Files
nihms149287.pdf
Additional details
Identifiers
- PMCID
- PMC2783583
- Eprint ID
- 16644
- Resolver ID
- CaltechAUTHORS:20091110-131044509
Funding
- NIH
- RO1 GM073932
- Bristol-Myers Squibb
- Novartis
- Army Research Office (ARO)
- Office of Naval Research (ONR)
Dates
- Created
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2009-11-16Created from EPrint's datestamp field
- Updated
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2021-11-08Created from EPrint's last_modified field