5422-47-9Relevant articles and documents
Intermolecular oxyarylation of olefins with aryl halides and TEMPOH catalyzed by the phenolate anion under visible light
Li, Xipan,Liang, Kangjiang,Liu, Qian,Shen, Lei,Wei, Delian,Xia, Chengfeng,Zheng, Liyan
, p. 6996 - 7002 (2020/07/23)
The phenolate anion was discovered as a new photocatalyst with strong reduction potentials. Under visible light irradiation, the phenolate anion enabled the reduction of (hetero)aryl halides (including electron-rich aryl chlorides) to (hetero)aryl radicals through single electron transfer. Based on this new photocatalyst, a novel and efficient photocatalytic protocol for the intermolecular oxyarylation of olefins with aryl halides and TEMPOH was developed. The developed three-component coupling reaction proceeded under redox-neutral reaction conditions with stable and readily available synthons and exhibited broad substrate scope. The utility of this process was further highlighted by the diversified chemical manipulation of the resulting oxyarylation products and the late-stage modification of active pharmaceutical ingredients.
Nitrogen Dioxide Catalyzed Aerobic Oxidative Cleavage of C(OH)–C Bonds of Secondary Alcohols to Produce Acids
Liu, Mingyang,Zhang, Zhanrong,Song, Jinliang,Liu, Shuaishuai,Liu, Huizhen,Han, Buxing
supporting information, p. 17393 - 17398 (2019/11/11)
Stable organic nitroxyl radicals are an important class of catalysts for oxidation reactions, but their wide applications are hindered by their steric hinderance, high cost, complex operation, and separation procedures. Herein, NO2 in DMSO is shown to effectively catalyze the aerobic oxidative cleavage of C(OH)?C bonds to form a carboxylic group, and NO2 was generated in situ by decomposition of nitrates. A diverse range of secondary alcohols were selectively converted into acids in excellent yields in this transition-metal-free system without any additives. Preliminary results also indicate its applicability to depolymerize recalcitrant macromolecular lignin. Detail studies revealed that NO2 from nitrates promoted the reaction, and NO2 served as hydrogen acceptor and radical initiator for the tandem oxidative reaction.
Chemoselective Benzylation of Aldehydes Using Lewis Base Activated Boronate Nucleophiles
Hollerbach, Michael R.,Barker, Timothy J.
, p. 1425 - 1427 (2018/05/24)
A benzylation of aldehydes using primary and secondary benzylboronic acid pinacol esters is reported. Activation of the boronic ester with s-butyllithium rendered it nucleophilic toward aldehydes. The activated nucleophile chemoselectively transfers the benzyl group over the sec-butyl group, providing excellent yields of the benzylated products. 11B NMR experiments were performed to study the mechanism of this transformation.