37069-08-2Relevant articles and documents
Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling
Liu, Chengwei,Ji, Chong-Lei,Zhou, Tongliang,Hong, Xin,Szostak, Michal
supporting information, p. 10690 - 10699 (2021/04/09)
Cooperative bimetallic catalysis is a fundamental approach in modern synthetic chemistry. We report bimetallic cooperative catalysis for the direct decarbonylative heteroarylation of ubiquitous carboxylic acids via acyl C-O/C-H coupling. This novel catalytic system exploits the cooperative action of a copper catalyst and a palladium catalyst in decarbonylation, which enables highly chemoselective synthesis of important heterobiaryl motifs through the coupling of carboxylic acids with heteroarenes in the absence of prefunctionalization or directing groups. This cooperative decarbonylative method uses common carboxylic acids and shows a remarkably broad substrate scope (>70 examples), including late-stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to gain insight into the mechanism of the reaction. The key step involves intersection of the two catalytic cycles via transmetallation of the copper–aryl species with the palladium(II) intermediate generated by oxidative addition/decarbonylation.
Direct C—H Bond Activation of Benzoxazole and Benzothiazole with Aryl Bromides Catalyzed by Palladium(II)-N-heterocyclic Carbene Complexes
Kalo?lu, Murat,Kalo?lur, Nazan,?zdemir, ?smail
, p. 837 - 844 (2018/07/31)
Herein, we report that a series of novel palladium(II)-NHC complexes (NHC=N-heterocyclic carbene) were synthesized. The structures of all novel complexes were characterized by 1H NMR, 13C NMR, FT-IR spectroscopy and elemental analysis techniques. These palladium(II)-NHC complexes were tested as efficient catalysts in the direct C—H bond activation of benzoxazole and benzothiazole with aryl bromides in the presence of 1 mol% catalyst loading at 150 °C for 4 h. Under the given conditions, various aryl bromides were successfully applied as the arylating reagents to achieve the 2-arylbenzoxazoles and 2-arylbenzothiazoles in acceptable to high yields.
High-Throughput Screening Protocol for the Coupling Reactions of Aryl Halides Using a Colorimetric Chemosensor for Halide Ions
Eom, Min Sik,Noh, Jieun,Kim, Han-Sung,Yoo, Soyeon,Han, Min Su,Lee, Sunwoo
supporting information, p. 1720 - 1723 (2016/05/19)
Mercury complex of 4-(2-pyridylazo)resorcinol (PAR-2Hg2+), a halide-ion chemosensor, was prepared and its efficiency as a tool for high-throughput screening (HTS) of transition-metal-catalyzed coupling reactions was investigated. It showed a high selectivity for halide ions. When the PAR-2Hg2+ complex was used in the Suzuki coupling reaction and C-H activated coupling reaction with aryl bromides, the quantitative and qualitative conversions of aryl halides were obtained from the reaction mixture color change.