N-Aminopyridinium Ylide-Directed, Copper-Promoted Amination of sp2C–H Bonds

N-Aminopyridinium ylides are used as monodentate directing groups for copper-promoted C–H/N–H coupling of sp2C–H bonds with pyrazoles, imidazoles, and sulfonamides. Reactions proceed in fluorinated alcohol solvents at elevated temperatures and require use of 1.3–3 equiv of copper(II) acetate. This appears to be the first method for copper-promoted C–H/N–H coupling directed by a removable monodentate auxiliary in absence of added ligands.