Electrophilic trifluoromethylation of arenes and N-heteroarenes using hypervalent iodine reagents
Electrophilic trifluoromethylation of arenes and N-heteroarenes using hypervalent iodine reagents
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DOI：
10.1016/j.jfluchem.2010.06.020
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发表时间：
2010-09-01
影响因子：
1.9
通讯作者：
Togni, Antonio
中科院分区：
文献类型：
--
作者：
Wiehn, Matthias S.;Vinogradova, Ekaterina V.;Togni, Antonio
高价碘三氟甲基化试剂与各种芳烃和N-杂芳烃反应，得到相应的三氟甲基化化合物。在比较研究中，1-三氟甲基-1，3-二氢-3，3-二甲基-1，2-苯碘杂环戊烯（2）被证明是上级于1-三氟甲基-1，2-苯碘杂环戊烯-3-（（1）H）-酮（1）的直接芳族三氟甲基化反应。根据个别基板，添加剂，如锌双（三氟甲基磺酰基）亚胺或三（三甲基甲硅烷基）甲硅烷基氯证明有助于促进反应。在氮杂环的情况下，观察到在与氮相邻的位置处并入三氟甲基的显著趋势。(C)2010 Elsevier BV保留所有权利。
The reaction of hypervalent iodine trifluoromethylating reagents with a variety of arenes and N-heteroarenes gives access to the corresponding trifluoromethylated compounds. In comparative studies, 1-trifluoromethyl-1,3-dihydro-3,3-dimethyl-1.2-benziodoxole (2) proved to be the superior to 1-trifluoromethyl-1,2-benziodoxol-3-((1)H)-one (1) for the direct aromatic trifluoromethylation. Depending on the individual substrates, additives such as zinc bis(trifluoromethylsulfonyl)imide or tris(trimethylsilyl)silyl chloride proved helpful in promoting the reactions. In the case of nitrogen heterocycles a pronounced tendency for the incorporation of the trifluoromethyl group at the position adjacent to nitrogen was observed. (C) 2010 Elsevier B.V. All rights reserved.