One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents.
One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents.
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DOI：
10.1021/jacs.9b04606
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发表时间：
2019-06
影响因子：
15
通讯作者：
Xiao Xiao-Xiao;T. Hoye
中科院分区：
文献类型：
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作者：
Xiao Xiao-Xiao;T. Hoye
在这里，我们公开了一种用于萘形成的级联策略，其利用传统的苯炔生成（即，来自邻甲硅烷基芳基三氟甲磺酸酯）和热六氢-狄尔斯-桤木（HDDA）反应。在这种转变中，三种不同的芳炔物种串联工作，其中两种可以被正式认为是1，2-联苯炔，并且每种都经历了不同类型的捕获事件。通过改变萘捕获化学以及1，2-苯二炔当量来探索许多实例。这种策略可以快速构建各种萘产物，并具有合成扩展多环芳烃的潜力。
Here we disclose a cascade strategy for naphthyne formation that capitalizes on the traditional benzyne generation (i.e., from an ortho-silyl aryl triflate) and the thermal hexadehydro-Diels-Alder (HDDA) reaction. In this transformation, three distinct aryne species work in tandem, two of which can be formally considered as a 1,2-benzidyne, and each undergoes a different type of trapping event. Many examples were explored by varying the naphthyne capture chemistry as well as the 1,2-benzdiyne equivalent. This strategy enables rapid construction of various naphthalene products and has potential for the synthesis of extended polycyclic arenes.