Site‐Selective C−H Functionalization of Carbazoles
Site‐Selective C−H Functionalization of Carbazoles
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咔唑的位点选择性 C-H 官能化
DOI：
10.1002/anie.202303110
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发表时间：
2023
期刊：
影响因子：
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通讯作者：
Ge, Haibo
中科院分区：
文献类型：
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作者：
Elsaid, Mazen;Ge, Robbie;Liu, Chong;Maiti, Debabrata;Ge, Haibo
咔唑类生物碱在药物和材料科学中具有巨大的应用潜力。然而，目前用于咔唑的C1官能化的方法依赖于使用预先安装的导向基团，严重限制了它们的适用性并阻碍了它们的整体效率。在此，我们首次报道了直接Pd催化的咔唑C-H烷基化和酰化反应的发展，并以顺丁烯二烯（NBE）作为瞬态定向介体。值得注意的是，在这种情况下，提出了六元钯中间体的参与，代表了广泛研究的Pd/α-烯烃反应领域中这种中间体的第一个例子。
Carbazole alkaloids hold great potential in pharmaceutical and material sciences. However, the current approaches for C1 functionalization of carbazoles rely on the use of a pre‐installed directing group, severely limiting their applicability and hindering their overall efficiency. Herein, we report for the first time the development of direct Pd‐catalyzed C−H alkylation and acylation of carbazoles assisted by norbornene (NBE) as a transient directing mediator. Notably, the involvement of a six‐membered palladacycle intermediate was suggested in this case, representing the first example of such intermediacy within the extensively studied Pd/norbornene reactions realm.