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Phenylenediamine catalysis of "click glycosylations" in water: practical and direct access to unprotected

Aurélie Baron1, Yves Blériot, Matthieu Sollogoub

  • 1CNRS and Univ Paris Sud, Glycochimie Moléculaire et Macromoléculaire, ICMMO, UMR 8182, Orsay, F-91405, France.

Organic & Biomolecular Chemistry
|May 16, 2008
PubMed

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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...