title: Direct intermolecular aniline ortho-arylation via benzyne intermediates.
abstract: A method for direct, transition-metal-free ortho-arylation of anilines by aryl chlorides, bromides, fluorides, and triflates has been developed. This methodology provides the most direct approach to 2-arylanilines since no protecting or directing groups on nitrogen are required. The arylation is functional-group tolerant, with alkene, ether, trifluoromethyl, dimethylamino, carbonyl, chloro, and cyano functionalities tolerated. Phenylation of enantiopure binaphthyldiamine affords a product with >99% ee.
authors.affiliation: Department of Chemistry, University of Houston, Houston, Texas 77204-5003, USA.
authors.forename: Thanh
authors.initials: T
authors.lastname: Truong
authors.forename: Olafs
authors.initials: O
authors.lastname: Daugulis
mesh_terms: D015081:2-Naphthylamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000814:Aniline Compounds; D001555:Benzene Derivatives; C524146:benzyne; D015081:2-Naphthylamine