Cyclization of 1-ethynyl-2-alkenylbenzenes to naphthalenes using Et2AlCl and DIBAL-H
作者:Yuma Nonoyama、Kazuki Yaguchi、Hidenori Kinoshita、Katsukiyo Miura
DOI:10.1016/j.tetlet.2020.152682
日期:2021.1
A one-pot procedure has been developed for the synthesis of substituted naphthalenes from 1-ethynyl-2-alkenylbenzenes. The successive reaction of a variety of 1-ethynyl-2-alkenylbenzenes with BuLi, Et2AlCl, and diisobutylaluminum hydride (DIBAL-H) in one pot gives the corresponding substituted naphthalenes in excellent yields. β, β-Bisaluminated styrenes, which are generated in situ, undergo an intramolecular
已经开发了一种一锅法用于从1-乙炔基-2-烯基苯合成取代的萘。多种1-乙炔基-2-烯基苯与BuLi,Et 2 AlCl和二异丁基氢化铝(DIBAL-H)的连续反应在一个罐中得到相应的取代萘,收率很高。原位生成的β,β-双歧化的苯乙烯分子发生分子内环化反应,形成氧化铝。萘铝中间体可以用甲醇d 4捕集形成氘化产物,这提供了一些机理上的见识。通过用N-碘代琥珀酰亚胺(NIS)和碘淬灭萘铝,也可获得相应的碘化萘。