The Development of a Palladium-Catalyzed Tandem Addition/Cyclization for the Construction of Indole Skeletons
The Development of a Palladium-Catalyzed Tandem Addition/Cyclization for the Construction of Indole Skeletons
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用于构建吲哚骨架的钯催化串联加成/环化的发展
DOI：
10.1021/acs.joc.7b00148
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发表时间：
2017
影响因子：
3.6
通讯作者：
Huayue Wu
中科院分区：
文献类型：
--
作者：
Shuling Yu;Linjun Qi;Kun Hu;Julin Gong;Tianxing Cheng;Qingzong Wang;Jiuxi Chen;Huayue Wu
首次开发了钯催化2-(2-氨基芳基)乙腈与芳基硼酸的串联加成/环化反应，实现了直接构建吲哚骨架的新策略。该系统表现出良好的官能团耐受性和显着的化学选择性。特别是，卤素（例如溴和碘）取代基易于进一步合成，从而扩大了产品的多样性。初步机制实验表明，这种转化涉及顺序亲核加成，然后是分子内环化。
A palladium-catalyzed tandem addition/cyclization of 2-(2-aminoaryl)acetonitriles with arylboronic acids has been developed for the first time, achieving a new strategy for direct construction of indole skeletons. This system shows good functional group tolerance and remarkable chemoselectivity. In particular, the halogen (e.g., bromo and iodo) substituents are amenable to further synthetic elaborations thereby broadening the diversity of the products. Preliminary mechanistic experiments indicate that this transformation involves sequential nucleophilic addition followed by an intramolecular cyclization.