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Catalytic C−H Bond Functionalization with Palladium(II): Aerobic Oxidative Annulations of Indoles

Ferreira, Eric M. and Stoltz, Brian M. (2003) Catalytic C−H Bond Functionalization with Palladium(II): Aerobic Oxidative Annulations of Indoles. Journal of the American Chemical Society, 125 (32). pp. 9578-9579. ISSN 0002-7863. doi:10.1021/ja035054y. https://resolver.caltech.edu/CaltechAUTHORS:20170216-082726177

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Abstract

A palladium-catalyzed aerobic oxidative annulation of indoles is described. We have demonstrated that a variety of factors influence these cyclizations, and in particular the electronic nature of the pyridine ligand is crucial. It is also remarkable that these oxidative cyclizations can proceed in good yield despite background oxidative decomposition pathways, testament to the facile nature with which molecular oxygen can serve as the direct oxidant for Pd(0). We have also shown that the mechanism most likely involves initial indole palladation (formal C−H bond activation) followed by migratory insertion and β-hydrogen elimination.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja035054yDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja035054yPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja035054yRelated ItemSupporting Information
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2003 American Chemical Society. Received 7 March 2003. Published online 22 July 2003. Published in print 1 August 2003. We thank the NIH-NIGMS (GM65961-01) and the NSF (predoctoral fellowship to E.M.F.) for generous financial support, and Professors András Kotschy and Greg Fu for stimulating discussions.
Funders:
Funding AgencyGrant Number
NIHGM65961-01
NSF Predoctoral FellowshipUNSPECIFIED
Issue or Number:32
DOI:10.1021/ja035054y
Record Number:CaltechAUTHORS:20170216-082726177
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170216-082726177
Official Citation:Catalytic C−H Bond Functionalization with Palladium(II):  Aerobic Oxidative Annulations of Indoles Eric M. Ferreira and Brian M. Stoltz Journal of the American Chemical Society 2003 125 (32), 9578-9579 DOI: 10.1021/ja035054y
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:74363
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:16 Feb 2017 17:07
Last Modified:11 Nov 2021 05:26

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