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


ABSTRACT: 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.

SUBMITTER: Irving CD 

PROVIDER: S-EPMC10195045 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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Synthesis of Imide and Amine Derivatives via Deoxyamination of Alcohols Using <i>N</i>-Haloimides and Triphenylphosphine.

Irving Charles D CD   Floreancig Jack T JT   Gasonoo Makafui M   Kelley Alexandra S AS   Laulhé Sébastien S  

ChemistrySelect 20210906 33


A deoxyamination methodology of activated and unactivated alcohols is presented. The reaction is mediated by phosphonium intermediates generated <i>in situ</i> from <i>N</i>-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. ...[more]

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