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On the Impact of Steric and Electronic Properties of Ligands on Gold(I)-Catalyzed Cycloaddition Reactions

Benitez, Diego and Tkatchouk, Ekaterina and Gonzalez, Ana Z. and Goddard, William A., III and Toste, F. Dean (2009) On the Impact of Steric and Electronic Properties of Ligands on Gold(I)-Catalyzed Cycloaddition Reactions. Organic Letters, 11 (21). pp. 4798-4801. ISSN 1523-7060. PMCID PMC2783583. https://resolver.caltech.edu/CaltechAUTHORS:20091110-131044509

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ol9018002 DOIArticle
http://pubs.acs.org/doi/full/10.1021/ol9018002PublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2783583PubMed CentralArticle
ORCID:
AuthorORCID
Goddard, William A., III0000-0003-0097-5716
Toste, F. Dean0000-0001-8018-2198
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.
Funders:
Funding AgencyGrant Number
NIHRO1 GM073932
Bristol-Myers SquibbUNSPECIFIED
NovartisUNSPECIFIED
Army Research Office (ARO)UNSPECIFIED
Office of Naval Research (ONR)UNSPECIFIED
Issue or Number:21
PubMed Central ID:PMC2783583
Record Number:CaltechAUTHORS:20091110-131044509
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20091110-131044509
Official Citation:On the Impact of Steric and Electronic Properties of Ligands on Gold(I)-Catalyzed Cycloaddition Reactions Diego Benitez, Ekaterina Tkatchouk, Ana Z. Gonzalez, William A. Goddard III, F. Dean Toste Organic Letters 2009 11 (21), 4798-4801
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:16644
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:16 Nov 2009 22:25
Last Modified:28 Oct 2019 18:20

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