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Direct Generation of Oxygen-Stabilized Radicals by H• Transfer from Transition Metal Hydrides

Kuo, Jonathan L. and Hartung, John and Han, Arthur and Norton, Jack R. (2015) Direct Generation of Oxygen-Stabilized Radicals by H• Transfer from Transition Metal Hydrides. Journal of the American Chemical Society, 137 (3). pp. 1036-1039. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20150313-103641415

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Abstract

Transition-metal hydrides generate α-alkoxy radicals by H• transfer to enol ethers. We have measured the rate constant for transfer from CpCr(CO)_3H to n-butyl vinyl ether and have examined the chemistry of radicals generated by such transfers. Radicals from appropriate substrates undergo 5-exo cyclization, with higher diastereoselectivity than the analogous all-carbon radicals. From such radicals it is straightforward to make substituted tetrahydrofurans.


Item Type:Article
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URLURL TypeDescription
http://dx.doi.org/10.1021/ja511883bDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja511883bPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja511883bPublisherSupporting Information
ORCID:
AuthorORCID
Han, Arthur0000-0001-8691-699X
Additional Information:© 2015 American Chemical Society. Received: November 19, 2014; Published: January 8, 2015. This material is based upon work supported by the National Science Foundation under Grant No. CHE-1401049 (IUPAC Novel Molecular and Supramolecular Theory and Synthesis Approaches for Sustainable Catalysis). J.L.K. acknowledges the National Science Foundation Graduate Research Fellowship Program. The authors are grateful to Scott A. Snyder, Deven P. Estes, and Gang Li for helpful discussions. Kevin D. Vo is acknowledged for the synthesis of starting materials.
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Funding AgencyGrant Number
NSFCHE-1401049
NSF Graduate Research FellowshipUNSPECIFIED
Issue or Number:3
Record Number:CaltechAUTHORS:20150313-103641415
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20150313-103641415
Official Citation:Direct Generation of Oxygen-Stabilized Radicals by H• Transfer from Transition Metal Hydrides Jonathan L. Kuo, John Hartung, Arthur Han, and Jack R. Norton Journal of the American Chemical Society 2015 137 (3), 1036-1039 DOI: 10.1021/ja511883b
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:55745
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:13 Mar 2015 19:38
Last Modified:03 Oct 2019 08:08

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