Regioselective Ruthenium-Catalyzed Carbonylative Direct Arylation of Five-Membered and Condensed Heterocycles

• Published in: Chemistry : a European journal Vol. 20; no. 11; pp. 3135 - 3141
• Main Authors: Pospech, Jola, Tlili, Anis, Spannenberg, Anke, Neumann, Helfried, Beller, Matthias
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 10.03.2014; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Aqueous solutions; Biocompatibility; Bonding; carbonylative coupling; Carbonyls; Catalysis; Chemistry; Chemistry, Multidisciplinary; Condensing; CH bond functionalization; heterocycles; Heterocyclic Compounds - chemistry; Hydrogen Bonding; Ketones; Ketones - chemistry; multicomponent reactions; Physical Sciences; ruthenium; Ruthenium - chemistry; Science & Technology; Synthesis; Transformations; multicomponent reactions; ACTIVATION; carbonylative coupling; C-H BOND; CROSS-COUPLING REACTION; DIARYL KETONES; ALDEHYDES; CH bond functionalization; FUNCTIONALIZATION; ruthenium; ACYL CHLORIDES; heterocycles; ARYL KETONES; PHOSPHINE OXIDES; HECK REACTION; CH bond functionalization
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201304314

A ruthenium‐catalyzed carbonylative CH bond arylation process for the three‐component synthesis of complex aryl–(hetero)aryl ketones in an aqueous solution has been developed. By exploiting the ortho‐activating effect of nitrogen‐containing directing groups, a regioselective, successive twofold C(sp2)C(sp2) bond formation has been achieved. This straightforward catalytic process provides access to versatile products prevalent in multiple bioactive compounds and supplies a valuable functional group for subsequent transformations. CH bond functionalization: A ruthenium‐catalyzed carbonylative CH bond arylation process for the three‐component synthesis of complex aryl–(hetero)aryl ketones in an aqueous solution has been developed (see scheme). By exploiting the ortho‐activating effect of nitrogen‐containing directing groups, a regioselective, successive twofold C(sp2)C(sp2) bond formation has been achieved.