title: New organocatalyst scaffolds with high activity in promoting hydrazone and oxime formation at neutral pH.
abstract: The discovery of two new classes of catalysts for hydrazone and oxime formation in water at neutral pH, namely 2-aminophenols and 2-(aminomethyl)benzimidazoles, is reported. Kinetics studies in aqueous solutions at pH 7.4 revealed rate enhancements up to 7-fold greater than with classic aniline catalysis. 2-(Aminomethyl)benzimidazoles were found to be effective catalysts with otherwise challenging aryl ketone substrates.
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305-5017, United States.
authors.forename: Dennis
authors.initials: D
authors.lastname: Larsen
authors.forename: Michael
authors.initials: M
authors.lastname: Pittelkow
authors.forename: Saswata
authors.initials: S
authors.lastname: Karmakar
authors.forename: Eric T
authors.initials: ET
authors.lastname: Kool
mesh_terms: D000627:Aminophenols / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry; D001562:Benzimidazoles / Q000737:chemistry*; D002384:Catalysis; D006835:Hydrazones / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry*
chemical_list: D000627:Aminophenols; D000814:Aniline Compounds; D001562:Benzimidazoles; D006835:Hydrazones; D007659:Ketones; D010091:Oximes; C023650:aniline