Direct Vicinal Difunctionalization of Thiophenes Enabled by the Palladium/Norbornene Cooperative Catalysis
Direct Vicinal Difunctionalization of Thiophenes Enabled by the Palladium/Norbornene Cooperative Catalysis
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DOI：
10.1021/jacs.9b10857
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发表时间：
2019-12-04
影响因子：
15
通讯作者：
Dong, Guangbin
中科院分区：
文献类型：
--
作者：
Li, Renhe;Zhou, Yun;Dong, Guangbin
在此，我们报道了通过钯/降冰片烯（Pd/NBE）协同催化，噻吩的直接邻域双功能化。一系列单取代和双取代噻吩可以在C4和CS位置选择性地和区域选择性地双功能化，产量很高，这是由一个砷配体和一个独特的基于酰胺的NBE实现的。合成用途已在复杂生物活性化合物的衍生化和开瓶克级制备中得到证明。在呋喃的双官能化和2-取代噻吩的直接c4选择性芳基化方面取得了初步结果。
Herein we report a direct vicinal difunctionalization of thiophenes via the palladium/norbornene (Pd/NBE) cooperative catalysis. A series of mono- and disubstituted thiophenes can be difunctionalized site-selectively and regioselectively at the C4 and CS positions in good yields, enabled by an arsine ligand and a unique amide-based NBE. The synthetic utility has been shown in derivatizations of complex bioactive compounds and an open-flask gram-scale preparation. Preliminary results have been obtained in the difunctionalization of furans and a direct C4-selective arylation of 2-substituted thiophenes.