Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of amines
Transition-metal-free catalysis enables the opening of aziridines and azetidines using alkenyl, alkynyl, or aryl/heteroaryl trifluoroborate salts to provide β,β- and γ,γ-substituted amines with complete regioselectivity and high diastereoselectivity.
T. Liu, Y. Li, L. Lai, J. Cheng, J. Sun, J. Wu, Org. Lett., 2018, 20, 3605-3608.
Palladium-catalyzed reductive cross-coupling reaction of various protected allylic amine derivatives with alkylzinc reagents yields anti-Markovnikov products. Preliminary mechanistic studies suggest that a reversible β-hydride elimination/hydride insertion process furnishes the primary Pd-alkyl intermediate, which then undergoes transmetalation followed by reductive elimination.
R. J. DeLuca, M. S. Sigman, J. Am. Chem. Soc., 2011, 133, 11454-11457.