title: Regioselective radical arylation of anilines with arylhydrazines.
abstract: Substituted 2-aminobiphenyls have been prepared from arylhydrazines and anilines via radical arylation reactions under simple oxidative conditions. The strong directing effect of the free and unprotonated amino functionality leads to high regioselectivities, and anilines have been shown to be significantly better aryl radical acceptors than nitrobenzenes or phenyl ethers. The methodology is also applicable to phenols, which react best as phenolates under strongly basic conditions. Finally, radical arylation reactions of anilines and anilinium salts under various conditions have for the first time demonstrated that regioselectivity can also be controlled through the rearomatization step and that the addition of an aryl radical to a substituted benzene might even be reversible.
authors.affiliation: Department of Chemistry and Pharmacy, Pharmaceutical Chemistry, Friedrich-Alexander-Universität Erlangen-Nürnberg, Schuhstraße 19, 91052 Erlangen, Germany.
authors.forename: Hannelore
authors.initials: H
authors.lastname: Jasch
authors.forename: Julia
authors.initials: J
authors.lastname: Scheumann
authors.forename: Markus R
authors.initials: MR
authors.lastname: Heinrich
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D006834:Hydrazines / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010647:Phenyl Ethers / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000814:Aniline Compounds; D006834:Hydrazines; D010647:Phenyl Ethers; D010165:Palladium; C023650:aniline