73351-22-1Relevant articles and documents
Mechanistic Insights into the FeCl3-Catalyzed Oxidative Cross-Coupling of Phenols with 2-Aminonaphthalenes
Vershinin, Vlada,Forkosh, Hagit,Ben-Lulu, Mor,Libman, Anna,Pappo, Doron
, p. 79 - 90 (2020/12/23)
The selective FeCl3-catalyzed oxidative cross-coupling reaction between phenols and primary, secondary, and tertiary 2-aminonaphthalene derivatives was investigated. The generality of this scalable method provides a sustainable alternative for preparing N,O-biaryl compounds that are widely used as ligands and catalysts. Based on a comprehensive kinetic investigation, a catalytic cycle involving a ternary complex that binds to both the coupling partners and the oxidant during the key oxidative coupling step is postulated. Furthermore, the studies showed that the reaction is regulated by off-cycle acid-base and ligand exchange processes.
Design and Atroposelective Construction of IAN analogues by Organocatalytic Asymmetric Heteroannulation of Alkynes
Shen, Jiahua,Tan, Bin,Wang, Yong-Bin,Wu, San,Zhang, Lei,Zhong, Guofu
supporting information, p. 23077 - 23082 (2020/10/19)
An organocatalytic atroposelective strategy for accessing enantioenriched axially chiral IAN analogues was developed for the first time. A class of novel atropisomeric C2-arylquinoline skeletons were synthesized with high enantiocontrol via chiral phosphoric-acid-catalyzed heteroannulation of in situ generated vinylidene ortho-quinone methide (VQM) intermediates with ortho-aminophenones. The strategy tolerated a broad substrate scope, providing a facile organocatalytic approach to IAN analogues in good yields and excellent enantioselectivities under mild reaction conditions. Moreover, the synthetic utility of this methodology was illustrated through further transformations into IAN-type ligand and axially chiral thiourea.
Double C-S bond formation: Via C-H bond functionalization: Synthesis of benzothiazoles and naphtho[2,1- d] thiazoles from N -substituted arylamines and elemental sulfur
Zhu, Xiaoming,Yang, Yuzhong,Xiao, Genhua,Song, Jianxin,Liang, Yun,Deng, Guobo
supporting information, p. 11917 - 11920 (2017/11/06)
A novel, atom economic, and environmentally friendly method for the synthesis of 2-substituted benzothiazoles and 2-substituted naphtho[2,1-d]thiazoles from N-substituted arylamines and elemental sulfur has been developed under metal-free conditions. The reaction underwent the process of double C-S bond formation through C-H bond functionalization.