66001-97-6Relevant articles and documents
Catalytic redox amidations of aldehydes with a polymer-supported peptide-N-heterocyclic carbene multifunctional catalyst
Gondo, Chenaimwoyo A.,Bode, Jeffrey W.
supporting information, p. 1205 - 1210 (2013/07/11)
We have prepared an oligomeric histidine-bound N-heterocyclic carbene precursor by coupling a carboxylic acid functionalized 1,2,4-triazolium salt to a peptide using solid-phase peptide synthesis. We have demonstrated that the resulting multifunctional resin-bound catalyst cooperatively facilitates redox amidation reactions of aldehydes and amines, a reaction not catalyzed by N-heterocyclic carbenes alone. Georg Thieme Verlag Stuttgart New York.
N-heterocyclic carbene-catalyzed redox amidations of α-functionalized aldehydes with amines
Bode, Jeffrey W.,Sohn, Stephanie S.
, p. 13798 - 13799 (2008/09/16)
A catalytic method for the direct synthesis of carboxylic acid amides from amines and α-functionalized aldehydes is possible through the synergistic role of a N-heterocyclic carbene catalyst and imidazole, affording amides via activated carboxylates catalytically generated via an internal redox reaction of the aldehyde substrates. The use of imidazole or other N-heterocycles as an additive is essential to overcoming imine formation and serves as a uniquely reactive substrate for the generation of an acyl imidazolium intermediate that is converted to the final amide product. Copyright
