65609-82-7Relevant academic research and scientific papers
A highly efficient metal-free approach to: Meta - And multiple-substituted phenols via a simple oxidation of cyclohexenones
Liang, Yu-Feng,Song, Song,Ai, Lingsheng,Li, Xinwei,Jiao, Ning
supporting information, p. 6462 - 6467 (2018/06/08)
A novel and efficient metal-free approach to substituted phenols has been disclosed from simple and readily available cyclohexenones and cyclohexenone equivalents. Dimethyl sulfoxide (DMSO), a simple and common organic reagent, was employed as a mild oxidant in this I2-catalysis, which significantly tolerates various substituents including some easily oxidizable or reducible functionalities. The challenging meta- and multiple-substituted phenols could be well prepared by this method. The metal-free and mild oxidation make this protocol very simple, practical, and easy to handle.
Iodine-Catalyzed Oxidative Aromatization: A Metal-Free Concise Approach to meta-Substituted Phenols from Cyclohex-2-enones
Wang, Shi-Ke,Chen, Ming-Tao,Zhao, Da-Yuan,You, Xia,Luo, Qun-Li
, p. 4093 - 4099 (2016/12/30)
A metal-free approach to meta-substituted phenols from cyclohex-2-enone via catalytic oxidative aromatization has been developed. The transformations are initiated with a catalytic amount of molecular iodine as the direct oxidant, while dimethyl sulfoxide is employed as the terminal oxidant. This practical approach is capable of avoiding the use of metal promoters and costly reagents, the lengthy synthesis, and overoxidation of products, and thus facilitates the efficient construction of meta-substituted phenol derivatives from inexpensive commercial chemicals under mild conditions. The synthetic utility of this approach is evident in the de novo syntheses of two bioactive molecules with good total yields, in which easily available chemicals were employed, protective groups were not utilized, and no unwanted carbon atoms were removed in each step. (Figure presented.).
