Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
Beilstein J Org Chem. 2010 Jun 16;6:65. doi: 10.3762/bjoc.6.65.
Since the discovery by Yagupolskii and co-workers that S-trifluoromethyl diarylsulfonium salts are effective for the trifluoromethylation of thiophenolates, the design and synthesis of electrophilic trifluoromethylating reagents have been extensively researched in both academia and industry, due to the significant unique features that trifluoromethylated compounds have in pharmaceuticals, agricultural chemicals, and functional materials. Several effective reagents have been developed by the groups of Yagupolskii, Umemoto, Shreeve, Adachi, Magnier, Togni and Shibata. Due to the high stability and reactivity of these reagents, a series of Umemoto reagents, Togni reagent and Shibata reagent are now commercially available. In this review, we wish to briefly provide a historical perspective of the development of so-called "shelf-stable electrophilic trifluoromethylating reagents", although this field is in constant development.
自 Yagupolskii 及其同事发现 S-三氟甲基二芳基锍盐可有效用于硫酚盐的三氟甲基化以来,由于三氟甲基化化合物在药物、农药和功能材料中具有显著的独特性质,学术界和工业界都在广泛研究设计和合成亲电三氟甲基化试剂。Yagupolskii、Umemoto、Shreeve、Adachi、Magnier、Togni 和 Shibata 等小组已经开发出了几种有效的试剂。由于这些试剂具有高稳定性和反应活性,一系列 Umemoto 试剂、Togni 试剂和 Shibata 试剂现已商品化。在本文综述中,我们希望简要介绍一下所谓的“稳定的亲电三氟甲基化试剂”的发展历史,尽管该领域还在不断发展。