959628-07-0Relevant academic research and scientific papers
Direct NHC-catalysed redox amidation using CO2 for traceless masking of amine nucleophiles
Davidson, Robert W. M.,Fuchter, Matthew J.
supporting information, p. 11638 - 11641 (2016/10/04)
The N-heterocyclic carbene (NHC)-catalysed redox amidation reaction is poorly developed and usually requires catalytic co-additives for electron-rich amine nucleophiles. We report a masking strategy (using CO2) that couples release of the free amine nucleophile to catalytic turnover, and in doing so, enables direct catalytic redox amidation of electron-rich amines.
Nucleophilic carbene and HOAt relay catalysis in an amide bond coupling: An orthogonal peptide bond forming reaction
Vora, Harit U.,Rovis, Tomislav
, p. 13796 - 13797 (2008/09/17)
A catalyzed internal redox process provides a route from α-reducible aldehydes and amines to α-reduced amides. The chemistry is catalyzed by nucleophilic carbenes and common peptide cocatalysts such as HOBt and HOAt in a relay fashion. The transformation proceeds in excellent yields using a variety of primary and secondary alkyl and aryl amines. The aldehyde component may be varied from haloaldehydes to epoxy and aziridino aldehydes as well as enals. The latter three substrates provide for a waste-free amide bond forming reaction. Copyright
