Published August 17, 2018
| Version Supplemental Material
Journal Article
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Radical Deoxychlorination of Cesium Oxalates for the Synthesis of Alkyl Chlorides
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1.
California Institute of Technology
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.
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.Attached Files
Supplemental Material - ol8b02045_si_001.pdf
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ol8b02045_si_001.pdf
Additional details
Identifiers
- Eprint ID
- 88374
- Resolver ID
- CaltechAUTHORS:20180731-110815223
Funding
- NSF Graduate Research Fellowship
- DGE-1144469
- American Cancer Society
- Heritage Medical Research Institute
- NSF
- CHE-1057143
Dates
- Created
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2018-07-31Created from EPrint's datestamp field
- Updated
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2021-11-16Created from EPrint's last_modified field
Caltech Custom Metadata
- Caltech groups
- Heritage Medical Research Institute