title: Remote Oxidation of Aliphatic C-H Bonds in Nitrogen-Containing Molecules.
abstract: Nitrogen heterocycles are ubiquitous in natural products and pharmaceuticals. Herein, we disclose a nitrogen complexation strategy that employs a strong Brønsted acid (HBF4) or an azaphilic Lewis acid (BF3) to enable remote, non-directed C(sp(3))-H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization.
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois, 61801, United States.
authors.forename: Jennifer M
authors.initials: JM
authors.lastname: Howell
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois, 61801, United States.
authors.forename: Kaibo
authors.initials: K
authors.lastname: Feng
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois, 61801, United States.
authors.forename: Joseph R
authors.initials: JR
authors.lastname: Clark
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois, 61801, United States.
authors.forename: Louis J
authors.initials: LJ
authors.lastname: Trzepkowski
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois, 61801, United States.
authors.forename: M Christina
authors.initials: MC
authors.lastname: White
mesh_terms: D002244:Carbon / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D002244:Carbon; D006859:Hydrogen; D009584:Nitrogen