Radical Deoxychlorination of Cesium Oxalates for the Synthesis of Alkyl Chlorides.

Org Lett

The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering , Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena , California 91125 , United States.

Published: August 2018

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.

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http://dx.doi.org/10.1021/acs.orglett.8b02045DOI Listing

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