Synthesis of Azo-Substituted Bicyclo[1.1.1]pentanes (BCPs) via Base-Promoted Halogen Atom Transfer,Organic Letters

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Synthesis of Azo-Substituted Bicyclo[1.1.1]pentanes (BCPs) via Base-Promoted Halogen Atom Transfer
Organic Letters ( IF 4.9 ) Pub Date : 2024-05-14 , DOI: 10.1021/acs.orglett.4c01546
Yanchuang Zhao ₁ , Jing Zhang ₁ , Zhi-Jin Zhan ₂ , Qiujin Fan ₁ , Xu-Qiong Xiao ₁ , Ying Bai ₁ , Shao-Fei Ni ₂ , Xinxin Shao ₁

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Because of the three-dimensional bioisosteric feature, bicyclo[1.1.1]pentylamines (BCPAs) are valuable scaffolds in synthetic chemistry and medicinal chemistry. Here, we report a Halogen Atom Transfer (XAT) mediated radical C–N coupling between C3-iodo-BCPs and diazonium salts in the presence of base. Similarly, a multicomponent reaction (MCR) enables the simultaneous construction of the C–C bond and C–N bond simultaneously. Versatile roles of diazonium salts were also explored.

中文翻译：

通过碱促进的卤素原子转移合成偶氮取代的双环[1.1.1]戊烷（BCP）

由于三维生物等排特征，双环[1.1.1]戊胺（BCPA）是合成化学和药物化学中有价值的支架。在这里，我们报告了在碱存在下，C3-碘-BCP 和重氮盐之间的卤素原子转移（XAT）介导的自由基 C-N 偶联。类似地，多组分反应（MCR）可以同时构建 C-C 键和 C-N 键。还探索了重氮盐的多功能作用。

更新日期：2024-05-14

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