Mild electrophilic trifluoromethylation of carbon- and sulfur-centered nucleophiles by a hypervalent iodine(III)-CF3 reagent
Mild electrophilic trifluoromethylation of carbon- and sulfur-centered nucleophiles by a hypervalent iodine(III)-CF3 reagent
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DOI：
10.1002/anie.200603497
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发表时间：
2007-01-01
影响因子：
16.6
通讯作者：
Togni, Antonio
中科院分区：
文献类型：
--
作者：
Kieltsch, Iris;Eisenberger, Patrick;Togni, Antonio
含氟和全氟烷基化有机化合物是学术界和工业界许多研究领域的重要目标。[1]最具挑战性的合成问题之一是以温和和选择性的方式引入三氟甲基。因此，可以在多步合成序列的后期实现的三氟甲基化反应仍然是非常受欢迎的。这些反应在经济上和生态上也应该是可行的。在这种情况下，使用更环保的CF3H代替CF3Br作为CF3合成子的主要来源是由Langlois和他的同事提出并成功实施的，用于制备新的亲核三氟甲基化试剂。[2]然而，最常用的亲核CF3来源仍然是(CH3)3SiCF3，它通常是由CF3Br.[3]另一方面，亲电三氟甲基化的使用要少得多，部分原因是合成A和B类经典试剂相对困难(方案1)。
Fluorinated and perfluoroalkylated organic compounds constitute important targets in many research fields both in academia and in industry.[1] One of the most challenging synthetic problems is the introduction of a trifluoromethyl group in a mild and selective manner. Thus, trifluoromethylation reactions that could be implemented at a late stage of a multistep synthetic sequence are still highly sought after. These reactions should also be economically and ecologically feasible. In this context, the use of the more environmentally friendly CF3H instead of CF3Br as a primary source of the CF3 synthon was proposed and implemented successfully by Langlois and co-workers for the preparation of new nucleophilic trifluoromethylation reagents.[2] However, the most commonly used nucleophilic CF3 source is still (CH3) 3SiCF3, which is usually prepared from CF3Br.[3] On the other hand, electrophilic trifluoromethylation is much less generally used, partly as a result of the relatively difficult synthetic access to the classical reagents of type A and B (Scheme 1).[4]