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Synthesis of Imide and Amine Derivatives via Deoxyamination of Alcohols Using N ‐Haloimides and Triphenylphosphine
Author(s) -
Irving Charles D.,
Floreancig Jack T.,
Gasonoo Makafui,
Kelley Alexandra S.,
Laulhé Sébastien
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202102296
Subject(s) - imide , triphenylphosphine , amine gas treating , chemistry , organic chemistry , polymer chemistry , catalysis
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.