17064-22-1Relevant 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.
Ni-Catalyzed C-H Arylation of Oxazoles and Benzoxazoles Using Pharmaceutically Relevant Aryl Chlorides and Bromides
Larson, Helen,Schultz, Danielle,Kalyani, Dipannita
, p. 13092 - 13103 (2019/10/17)
This manuscript details the development of the nickel-catalyzed arylation of oxazoles and benzoxazoles with aryl halides. A series of aryl, heteroaryl, and druglike electrophiles relevant to pharmaceutical applications were surveyed. The desired arylated products were obtained in synthetically useful yields using electronically and structurally varied aryl halides. The use of microscale high-throughput experimentation was essential for both the rapid identification of optimal reaction parameters and the investigation of the aryl halide scope.
CO2/Photoredox-Cocatalyzed Tandem Oxidative Cyclization of α-Bromo Ketones and Amines to Construct Substituted Oxazoles
Zhang, Xiaowei,He, Yonghui,Li, Jing,Wang, Rui,Gu, Lijun,Li, Ganpeng
, p. 8225 - 8231 (2019/06/17)
CO2/photoredox-cocatalyzed tandem oxidative cyclization of α-bromo ketones and amines for the preparation of substituted oxazoles has been achieved. The avoidance of using both transition-metal catalysts and peroxides makes this method more sustainable and renewable.