Laboratoire de Chimie Organique, Service de Chimie et Physico-Chimie Organiques, Université libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, 1050, Brussels, Belgium.
Chemistry. 2022 Jul 20;28(41):e202200975. doi: 10.1002/chem.202200975. Epub 2022 Jun 14.
Perfluoroalkylated (hetero)arenes represent an extremely important family of molecules commonly utilized in many areas such as medicinal chemistry, agrochemistry and material sciences. Due to their unique properties, they have attracted significant interest from synthetic chemists and various methods have been developed for their synthesis. Among them, the direct perfluoroalkylation of C(sp )-H bonds in (hetero)arenes is one of the most attractive and straightforward ones, provided that it proceeds with high levels of regioselectivity. In this review article, a comprehensive overview of advances in this field is presented, with a special focus on the reaction mechanisms involved in these transformations and their regioselectivity. All methods available have been classified according to the nature of the perfluoroalkyl chain introduced, trifluoromethylation reactions being overviewed in a separate section, and to the nature of the reagents/catalysts required.
全氟烷基化(杂)芳烃是一类非常重要的分子,广泛应用于医药化学、农业化学和材料科学等多个领域。由于其独特的性质,它们引起了合成化学家的极大兴趣,并且已经开发出了各种方法来合成它们。其中,(杂)芳环中 C(sp )-H 键的直接全氟烷基化是最具吸引力和直接的方法之一,只要它具有高区域选择性。在这篇综述文章中,全面介绍了该领域的进展,特别关注了这些转化的反应机制及其区域选择性。所有可用的方法都根据引入的全氟烷基链的性质进行了分类,三氟甲基化反应在单独的部分进行了综述,并根据所需试剂/催化剂的性质进行了分类。