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Transition‐Metal‐Free Trifluoromethylation of Benzyl Bromides Using Trifluoromethyltrimethylsilane and CsF in 1,2‐Dimethoxyethane
Asian Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-03-18 , DOI: 10.1002/ajoc.202000124
Kanako Nozawa‐Kumada 1 , Sayuri Osawa 1 , Takuto Ojima 1 , Koto Noguchi 1 , Masanori Shigeno 1 , Yoshinori Kondo 1
Affiliation  

An SN2‐type trifluoromethylation of benzyl halides under transition‐metal‐free conditions has been developed using trifluoromethyltrimethylsilane (CF3SiMe3, Ruppert−Prakash reagent) and CsF in 1,2‐dimethoxyethane (DME). Under the developed reaction conditions, the in situ generated trifluoromethyl anion (CF3) overcame the instability and displayed enhanced nucleophilicity in the presence of DME. This method provides an efficient approach for the generation of various (2,2,2‐trifluoroethyl)arenes such as those bearing alkyl, alkoxy, halo (F, Cl, and Br) and trifluoromethyl groups on the benzene rings.

中文翻译:

使用三氟甲基三甲基硅烷和CsF在1,2-二甲氧基乙烷中实现苄基溴的无过渡金属三氟甲基化

使用三氟甲基三甲基硅烷(CF 3 SiMe 3,Ruppert-Prakash试剂)和CsF在1,2-二甲氧基乙烷(DME)中开发了无过渡金属条件下的卤代甲烷S N 2型三氟甲基化。下发达反应条件下,在生成的三氟甲基阴离子(CF原位3 - )克服了不稳定性并显示增强的在DME的存在下亲核性。该方法为生成各种(2,2,2-三氟乙基)芳烃提供了一种有效的方法,例如在苯环上带有烷基,烷氧基,卤代(F,Cl和Br)和三氟甲基的芳烃。
更新日期:2020-03-18
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