化学
芳基
电子受体
电泳剂
三元运算
光化学
光催化
亲电取代
电子供体
卤化物
亲电芳香族取代
接受者
电子
药物化学
催化作用
有机化学
烷基
程序设计语言
物理
量子力学
计算机科学
凝聚态物理
作者
Jiayi Gu,Yingfen Meng,Zhuo Cheng,Guoqing Lu,Meixiu Xin,Jie Tang,Zhibo Du,Xuejing Zhang,Mingcai Deng,Yong Zou
标识
DOI:10.1016/j.xcrp.2024.102230
摘要
Highlights•Ternary EDA exciplex induced alkyl aryl ether synthesis•Aerobic EDA photocatalytic system•Good functional group compatibility and late-stage functionalization•Scalable synthesis of fine chemicalsSummaryThe direct use of molecular oxygen as a clean, abundant, and readily available reactant is one of the green, sustainable, yet challenging methodologies for C–O bond construction to access diverse oxygenated compounds. Herein, we report a ternary electron donor-acceptor complex photocatalytic system that utilizes O2 to construct multiple C–O bonds successively in a single-step operation, enabling the facile assembly of alkyl aryl ethers. Mechanistic investigation shows that the ternary aryl halide/2-tert-butyl-1,1,3,3-tetramethylguanidine/tetrahydrofuran exciplex generated in situ plays an essential role, affording a radical anion species that is captured by the electrophilic O2 to form a Meisenheimer-type intermediate, and subsequently participates in a Williamson etherification process to give ether products with good selectivity and compatibility. This protocol not only enables rapid access to alkyl aryl ethers but also allows the facile synthesis of fine chemicals, such as proparacaine, decylparaben, and sildenafil subunits, starting from readily available halogenated compounds.Graphical abstract
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