Modular Assembly of Spirocarbocyclic Scaffolds through Pd0- Catalyzed Intermolecular Dearomatizing [2+2+1] Annulation of Bromonaphthols with Aryl Iodides and Alkynes
Modular Assembly of Spirocarbocyclic Scaffolds through Pd0- Catalyzed Intermolecular Dearomatizing [2+2+1] Annulation of Bromonaphthols with Aryl Iodides and Alkynes
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通过 Pd-0 催化分子间脱芳构化进行螺碳环支架的模块化组装 [2 2 1] 溴萘酚与芳基碘化物和炔烃的环化
DOI：
10.1002/anie.201612127
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发表时间：
2017
期刊：
影响因子：
--
通讯作者：
Xinjun Luan
中科院分区：
文献类型：
--
作者：
Zhijun Zuo;Hui Wang;Liangxin Fan;Jingjing Liu;Yaoyu Wang;Xinjun Luan
以1-溴-2-萘酚为原料，通过钯（0）催化的[2+2+1]螺环化反应，快速合成了一系列螺[茚-1，1 ′-萘]-2 ′-酮。该三组分级联反应通过连续的Catellani-型C-H活化、不对称联芳基偶联、炔迁移插入和芳烃脱芳构化来实现。我们的方法的潜在效用是通过从炔系芳基碘和1-溴-2-萘酚的多环骨架的dalesconol A和B的一步构建来说明的。
A novel palladium(0)‐catalyzed dearomatizing [2+2+1] spiroannulation of 1‐bromo‐2‐naphthols with aryl iodides and alkynes was developed for the rapid assembly of spiro[indene‐1,1′‐naphthalen]‐2′‐ones. This three‐component cascade reaction was realized through consecutive Catellani‐type C−H activation, unsymmetrical biaryl coupling, alkyne migratory insertion, and arene dearomatization. The potential utility of our method is illustrated by the one‐step construction of the polycyclic skeletons of dalesconols A and B from alkyne‐tethered aryl iodides and 1‐bromo‐2‐naphthol.