Synthesis of Imide and Amine Derivatives via Deoxyamination of Alcohols Using N-Haloimides and Triphenylphosphine

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.

Automated summary

This deoxyamination methodology uses phosphonium intermediates generated in situ from N-haloimides and triphenylphosphine to mediate the reaction, allowing for the synthesis of phthalimide and amine derivatives in moderate to good yields at room temperature. NMR experiments have provided insight into the reactive intermediates involved and the mechanism of this deoxyamination reaction.