N-heterocyclic carbene catalyzed trifluoromethylation of carbonyl compounds
N-heterocyclic carbene catalyzed trifluoromethylation of carbonyl compounds
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DOI：
10.1021/ol050568i
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发表时间：
2005-05-26
期刊：
影响因子：
5.2
通讯作者：
Senanayake, CH
中科院分区：
文献类型：
--
作者：
Song, JJ;Tan, ZL;Senanayake, CH
发现了一种新型的N-杂环卡宾(NHC)催化的羰基化合物的三氟甲基化反应。可烯醇化和不可烯醇化的醛和α-酮酯在室温下与TMSCF3进行简单的三氟甲基化反应，仅在商业上可获得的NHC(1)的0.5-1摩尔%的存在下，以良好的产率提供CF3取代的醇。在NHC催化下，醛与酮的三氟甲基化反应可以实现。这些条件是温和和简单的，可以容忍各种官能团。
A novel N-heterocyclic carbene (NHC) catalyzed trifluoromethylation reaction of carbonyl compounds was discovered. Both enolizable and nonenolizable aldehydes and alpha-keto esters undergo facile trifluoromethylation with TMSCF3 at room temperature in the presence of only 0.5-1 mol % of the commercially available NHC (1), providing CF3-Substituted alcohols in good yields. Selective trifluoromethylation of aldehydes over ketones can be achieved under NHC catalysis. These conditions are mild and simple and tolerate a variety of functional groups.