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Synthesis of Imide and Amine Derivatives via Deoxyamination of Alcohols Using N-Haloimides and Triphenylphosphine. 2021
Charles D Irving, and
Jack T Floreancig, and
Makafui Gasonoo, and
Alexandra S Kelley, and
Sébastien Laulhé
Department of Chemistry and Chemical Biology Indiana University-Purdue University Indianapolis Indianapolis, IN 46202, United States.
A deoxyamination methodology of activated and unactivated alcohols is presented. The reaction is mediated by phosphonium intermediates generated in situ from N-haloimides and triphenylphosphine. The protocol allows for the synthesis of phthalimide and amine derivatives in moderate to good yields at room temperature. A series of NMR experiments have provided insight into the reactive intermediates involved and the mechanism of this deoxyamination reaction.
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