A catalytic, Brønsted base strategy for intermolecular allylic C-H amination.
A Brønsted base activation mode for oxidative, Pd(II)/sulfoxide-catalyzed, intermolecular C-H allylic amination is reported. N,N-diisopropylethylamine was found to promote amination of unactivated terminal olefins, forming the corresponding linear allylic amine products with high levels of stereo-, regio-, and chemoselectivity. The predictable and high selectivity of this C-H oxidation method enables late-stage incorporation of nitrogen into advanced synthetic intermediates and natural products.
Reed
Sean A
SA
Department of Chemistry, Roger Adams Laboratory, University of Illinois, Urbana, Illinois 61801, USA.
Mazzotti
Anthony R
AR
White
M Christina
MC
D000586:Amination; D001688:Biological Products / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry
D001688:Biological Products; D002219:Carbamates; D010165:Palladium; D002244:Carbon; D006859:Hydrogen