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Radical Deoxychlorination of Cesium Oxalates for the Synthesis of Alkyl Chlorides

Su, Justin Y. and Grünenfelder, Denise C. and Takeuchi, Kohei and Reisman, Sarah E. (2018) Radical Deoxychlorination of Cesium Oxalates for the Synthesis of Alkyl Chlorides. Organic Letters, 20 (16). pp. 4912-4916. ISSN 1523-7060. https://resolver.caltech.edu/CaltechAUTHORS:20180731-110815223

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Abstract

A radical deoxychlorination of cesium oxalates has been developed for the preparation of hindered secondary and tertiary alkyl chlorides. The reaction tolerates a number of functional groups, including ketones, alcohols, and amides, and provides complementary reactivity to standard deoxychlorination reactions proceeding by heterolytic mechanisms. Preliminary studies demonstrate that the developed conditions can also be applied to deoxybromination and deoxyfluorination reactions.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acs.orglett.8b02045DOIArticle
https://pubs.acs.org/doi/suppl/10.1021/acs.orglett.8b02045PublisherSupporting Information
ORCID:
AuthorORCID
Su, Justin Y.0000-0002-1946-3908
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2018 American Chemical Society. Received: June 29, 2018; Published: July 31, 2018. We thank Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We also thank Nicholas J. Fastuca for assistance in substrate preparation and Dr. Matthew J. Hesse for helpful discussions (both of Caltech). Fellowship support was provided by the National Science Foundation (graduate research fellowship to D.C.G., Grant No. DGE-1144469). S.E.R. is an American Cancer Society Research Scholar and Heritage Medical Research Institute Investigator. Financial support from the NSF (CAREER-1057143) is gratefully acknowledged. The authors declare no competing financial interest.
Group:Heritage Medical Research Institute
Funders:
Funding AgencyGrant Number
NSF Graduate Research FellowshipDGE-1144469
American Cancer SocietyUNSPECIFIED
Heritage Medical Research InstituteUNSPECIFIED
NSFCHE-1057143
Issue or Number:16
Record Number:CaltechAUTHORS:20180731-110815223
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180731-110815223
Official Citation:Radical Deoxychlorination of Cesium Oxalates for the Synthesis of Alkyl Chlorides Justin Y. Su, Denise C. Grünenfelder, Kohei Takeuchi, and Sarah E. Reisman Organic Letters 2018 20 (16), 4912-4916 DOI: 10.1021/acs.orglett.8b02045
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:88374
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:31 Jul 2018 18:24
Last Modified:03 Oct 2019 20:06

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