title: Pd-Catalyzed sequential β-C(sp(3))-H arylation and intramolecular amination of δ-C(sp(2))-H bonds for synthesis of quinolinones via an N,O-bidentate directing group.
abstract: The pharmacological importance of 2-quinolinone derivatives is well known. Herein, we developed an effective protocol for the synthesis of 2-quinolinone derivatives by palladium-catalyzed sequential β-C(sp(3))-H arylation and selective intramolecular C(sp(2))-H/N-H amination starting with aryl iodides and carboxylic acids. A novel directing group, glycine dimethylamide, was used in the synthesis. We synthesized various quinolinone derivatives, including 5-substituted quinolinones, which are difficult to obtain using the traditional pathway. The directing group could be easily removed and could be readily transformed into other useful functional groups.
authors.affiliation: Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, China. yszhao@suda.edu.cn.
authors.forename: Mingyu
authors.initials: M
authors.lastname: Guan
authors.affiliation: Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, China. yszhao@suda.edu.cn.
authors.forename: Yubo
authors.initials: Y
authors.lastname: Pang
authors.affiliation: Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, China. yszhao@suda.edu.cn.
authors.forename: Jingyu
authors.initials: J
authors.lastname: Zhang
authors.affiliation: College of Physics, Optoelectronics and Energy & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215006, China. jyzhang@suda.edu.cn.
authors.forename: Yingsheng
authors.initials: Y
authors.lastname: Zhao