title: Dual C-F, C-H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls.
abstract: Multifluorinated biaryls are challenging to synthesize and yet are an important class of molecules. Because of the difficulty associated with selective fluorination, this class of molecules represent a formidable synthetic challenge. An alternative approach to selective fluorination of biaryls is to couple an arene that already possesses C-F bonds in the desired location. This strategy has been regularly utilized and relies heavily on traditional cross-coupling strategies that employ organometallics and halides (or pseudohalides) in order to achieve the coupling. Herein we report conditions for the photocatalytic coupling via direct functionalization of the C-F bond of a perfluoroarene and C-H bond of the other arene to provide an expedient route to multifluorinated biaryls. The mild conditions and good functional group tolerance enable a broad scope, including access to the anti-Minisci product of basic heterocycles. Finally, we demonstrate the value of the C-F functionalization approach by utilizing the high fluorine content to systematically build complex biaryls containing between two and five Caryl-F bonds via the synergistic use of photocatalysis and SNAr chemistry.
authors.affiliation: Department of Chemistry, Oklahoma State University , Stillwater, Oklahoma 74078, United States.
authors.forename: Sameera
authors.initials: S
authors.lastname: Senaweera
authors.affiliation: Department of Chemistry, Oklahoma State University , Stillwater, Oklahoma 74078, United States.
authors.forename: Jimmie D
authors.initials: JD
authors.lastname: Weaver
mesh_terms: D001713:Biphenyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D055668:Photochemical Processes; D011725:Pyridines / Q000737:chemistry*
chemical_list: D001713:Biphenyl Compounds; D006845:Hydrocarbons, Fluorinated; D011725:Pyridines