title: Iron-Catalyzed Oxyfunctionalization of Aliphatic Amines at Remote Benzylic C-H Sites.
abstract: We report the development of an iron-catalyzed method for the selective oxyfunctionalization of benzylic C(sp(3))-H bonds in aliphatic amine substrates. This transformation is selective for benzylic C-H bonds that are remote (i.e., at least three carbons) from the amine functional group. High site selectivity is achieved by in situ protonation of the amine with trifluoroacetic acid, which deactivates more traditionally reactive C-H sites that are α to nitrogen. The scope and synthetic utility of this method are demonstrated via the synthesis and derivatization of a variety of amine-containing, biologically active molecules.
authors.affiliation: Department of Chemistry, University of Michigan , 930 North University Ave, Ann Arbor, Michigan 48109, United States.
authors.forename: Curren T
authors.initials: CT
authors.lastname: Mbofana
authors.affiliation: Department of Chemistry, University of Michigan , 930 North University Ave, Ann Arbor, Michigan 48109, United States.
authors.forename: Eugene
authors.initials: E
authors.lastname: Chong
authors.affiliation: Department of Chemistry, University of Michigan , 930 North University Ave, Ann Arbor, Michigan 48109, United States.
authors.forename: James
authors.initials: J
authors.lastname: Lawniczak
authors.affiliation: Department of Chemistry, University of Michigan , 930 North University Ave, Ann Arbor, Michigan 48109, United States.
authors.forename: Melanie S
authors.initials: MS
authors.lastname: Sanford
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D007501:Iron / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000588:Amines; D001593:Benzyl Compounds; D007501:Iron