title: Iridium-Catalyzed ortho-Arylation of Benzoic Acids with Arenediazonium Salts.
abstract: In the presence of catalytic [{IrCp*Cl2 }2 ] and Ag2 CO3 , Li2 CO3 as the base, and acetone as the solvent, benzoic acids react with arenediazonium salts to give the corresponding diaryl-2-carboxylates under mild conditions. This C-H arylation process is generally applicable to diversely substituted substrates, ranging from extremely electron-rich to electron-poor derivatives. The carboxylate directing group is widely available and can be removed tracelessly or employed for further derivatization. Orthogonality to halide-based cross-couplings is achieved by the use of diazonium salts, which can be coupled even in the presence of iodo substituents.
authors.affiliation: FB Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Strasse Geb. 54, 67663 Kaiserslautern (Germany).
authors.forename: Liangbin
authors.initials: L
authors.lastname: Huang
authors.affiliation: FB Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Strasse Geb. 54, 67663 Kaiserslautern (Germany).
authors.forename: Dagmar
authors.initials: D
authors.lastname: Hackenberger
authors.affiliation: FB Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Strasse Geb. 54, 67663 Kaiserslautern (Germany). goossen@chemie.uni-kl.de.
authors.forename: Lukas J
authors.initials: LJ
authors.lastname: Gooßen
mesh_terms: D001565:Benzoates / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003979:Diazonium Compounds / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D007495:Iridium / Q000737:chemistry*; D012492:Salts / Q000737:chemistry*
chemical_list: D001565:Benzoates; D003979:Diazonium Compounds; D006841:Hydrocarbons, Aromatic; D012492:Salts; D007495:Iridium
keywords: CH arylation; benzoic acid; biaryl synthesis; diazonium salts; iridium