title: Metal-free functionalization of N,N-dialkylanilines via temporary oxidation to N,N-dialkylaniline N-oxides and group transfer.
abstract: A simple set of protocols for the controlled elaboration of anilines is reported allowing access to a diverse array of aminophenols, aminoarylsulfonates, alkylated anilines, and aminoanilines in 29-95% yield in a single laboratory operation from easily isolable, bench-stable N,N-dialkylaniline N-oxides. The introduction of new C-O, C-C, and C-N bonds on the aromatic ring is made possible by a temporary increase in oxidation level and excision of a weak N-O bond.
authors.affiliation: Department of Chemistry, University of Hawaii at Manoa , 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States.
authors.forename: Robert S
authors.initials: RS
authors.lastname: Lewis
authors.forename: Michael F
authors.initials: MF
authors.lastname: Wisthoff
authors.forename: J
authors.initials: J
authors.lastname: Grissmerson
authors.forename: William J
authors.initials: WJ
authors.lastname: Chain
mesh_terms: D000478:Alkylation; D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010087:Oxides / Q000737:chemistry*
chemical_list: D000814:Aniline Compounds; D010087:Oxides