School of Chemistry and Chemical Engineering, Chongqing University, 174 Shazheng Street, Chongqing, P. R. China, 400030.
Chem Rev. 2021 Apr 14;121(7):3892-4044. doi: 10.1021/acs.chemrev.0c01011. Epub 2021 Feb 18.
Arynes are among the most active organic intermediates and have found numerous applications in expeditious preparation of substituted arenes. In the past 20 years, chemists have witnessed a resurgence in aryne chemistry, which is mainly attributed by the extensive utilization of Kobayashi's method, a fluoride-induced removal of the TMS group with concomitant departure of its OTf group on -silylaryl triflates. Nowadays, -silylaryl triflates are the most frequently employed aryne precursors. This review provides an overview of the history of Kobayashi's method, its methodological achievements, and its applications in the synthesis of natural products, bioactive molecules, and polycyclic aromatic hydrocarbons.
芳炔是最活跃的有机中间体之一,在取代芳烃的快速制备中得到了广泛的应用。在过去的 20 年中,化学家见证了芳炔化学的复兴,这主要归因于 Kobayashi 方法的广泛应用,该方法是通过氟化物诱导去除 TMS 基团,同时伴随其 OTf 基团从 -硅基芳基三氟甲磺酸酯上离去。如今,-硅基芳基三氟甲磺酸酯是最常用的芳炔前体。本文综述了 Kobayashi 方法的历史、方法学成就及其在天然产物、生物活性分子和多环芳烃合成中的应用。