三氟甲基化
化学
三氟甲基
有机化学
反应性(心理学)
硅烷化
亲核细胞
三甲基硅烷
乙醚
催化作用
溶剂
烷基
医学
病理
替代医学
作者
Rajendra Prasad Singh,Ganfeng Cao,Robert L. Kirchmeier,Jean’ne M. Shreeve
摘要
The low reactivity of carboxylic esters toward (trifluoromethyl)trimethylsilane (TMS−CF3) was investigated. A universal cesium fluoride catalyzed procedure for nucleophilic trifluoromethylation was developed. At room temperature (25 °C), with catalytic amounts of cesium fluoride, carboxylic esters were found to react to give the silyl ether intermediates, which afforded the trifluoromethyl ketones after hydrolysis. Sulfonic, sulfinic, and selenic esters also show good reactivity, giving novel trifluoromethylated compounds. The trifluoromethylation method was also applied to aldehydes and ketones, which were transformed to trifluoromethyl silyl ether intermediates and afforded trifluoromethylated alcohols in excellent yields after acid hydrolysis. Ethylene glycol dimethyl ether was used as solvent for solid or high boiling substrates, and benzonitrile was used for the low boiling substrates.
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