23000-31-9Relevant articles and documents
Chlorophyll-catalyzed photochemical regioselective coumarin C-H arylation with diazonium salts
Moazzam, Ali,Jafarpour, Farnaz
supporting information, p. 16692 - 16696 (2020/10/27)
This communication describes the development of a mild method for the cross-coupling of the C3-position of coumarin with an array of diazonium salts mediated by chlorophyll as a biocatalyst via visible light catalysis. A natural pigment such as chlorophyll is used as a green photosensitizer and environmentally benign catalyst. This general and easy procedure provides a transition-metal-free alternative for the formation of 3-aryl coumarin derivatives at room temperature with good to excellent yields. This journal is
Visible-light-driven copper-catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones and terminal alkynes: Regioselective synthesis of 3-arylcoumarins
Ragupathi, Ayyakkannu,Sagadevan, Arunachalam,Charpe, Vaibhav Pramod,Lin, Chun-Cheng,Hwu, Jih-Ru,Hwang, Kuo Chu
supporting information, p. 5151 - 5154 (2019/05/10)
We present the first example of sustainable, intuitive, highly regioselective, visible-light-driven copper catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones with terminal alkynes for the preparation of 3-arylcoumarins at room temperature. This operationally simple methodology has been successfully applied to a wide range of N-tosylhydrazones and alkynes (49 examples), and proceeds well to afford biologically active compounds, such as monoamine oxidase B (MAO-B) inhibitor and horseradish peroxidase (HRP) inhibitor, in satisfactory yields under mild conditions. Furthermore, mechanistic studies suggest that the reaction proceeds via a copper(ii)-superoxo or -peroxo complex mediated oxidative annulation of terminal alkynes, as evidenced by 18O2 isotopic-labelling experiments.
Regioselective C-3 arylation of coumarins with arylhydrazines via radical oxidation by potassium permanganate
Yuan, Jin-Wei,Li, Wei-Jie,Yang, Liang-Ru,Mao, Pu,Xiao, Yong-Mei
, p. 1115 - 1123 (2016/11/16)
An efficient protocol for oxidative C-3 arylation of coumarins with arylhydrazine has been developed using potassium permanganate as an oxidant. The arylated coumarins with different electronic properties were obtained in moderate to good yields. The deve