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CuCF3 mediated deoxyfluorination of redox-active esters
Journal of Fluorine Chemistry ( IF 1.7 ) Pub Date : 2023-03-12 , DOI: 10.1016/j.jfluchem.2023.110114
Zhenlei Zou , Wenju Chang , Weigang Zhang , Shengyang Ni , Yi Pan , Yong Liang , Donghui Pan , Yi Wang

Trifluoromethyl copper (CuCF3), as a diverse fluorination reagent, has been widely used in trifluoromethylation, perfluoroalkylation, and difluorocarbene reactions. However, it has rarely been reported as a single fluorine source involved in nucleophilic fluorination reactions. This work describes a general strategy involving copper-mediated deoxyfluorination of redox-active esters to rapidly access various aliphatic and aromatic acyl fluorides. The highly active CuF species could be generated from either copper fluoride salts or CuCF3. A plausible mechanism of CuCF3 forming an [F-CuCF2F5]- intermediate and NHBC ester forming acyl fluoride has been derived from DFT calculations.



中文翻译:

CuCF3 介导的氧化还原活性酯的脱氧氟化

三氟甲基铜(CuCF 3)作为一种多样化的氟化试剂,广泛应用于三氟甲基化、全氟烷基化和二氟卡宾反应。然而,它很少被报道为参与亲核氟化反应的单一氟源。这项工作描述了一种通用策略,涉及铜介导的氧化还原活性酯的脱氧氟化,以快速获得各种脂肪族和芳香族酰基氟。高活性的 CuF 物质可以从氟化铜盐或 CuCF 3中产生。CuCF 3形成[F-CuCF 2 F 5 ]-中间体和NHBC酯形成酰基氟的可能机制已从DFT计算推导出来。

更新日期:2023-03-12
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