Twofold Radical-Based Synthesis of N,C-Difunctionalized Bicyclo[1.1.1]pentanes,Journal of the American Chemical Society

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Twofold Radical-Based Synthesis of N,C-Difunctionalized Bicyclo[1.1.1]pentanes
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2021-06-23 , DOI: 10.1021/jacs.1c04180
Helena D Pickford ₁ , Jeremy Nugent ₁ , Benjamin Owen ₁ , James J Mousseau ₂ , Russell C Smith ₃ , Edward A Anderson ₁

Affiliation

Bicyclo[1.1.1]pentylamines (BCPAs) are of growing importance to the pharmaceutical industry as sp³-rich bioisosteres of anilines and N-tert-butyl groups. Here we report a facile synthesis of 1,3-disubstituted BCPAs using a twofold radical functionalization strategy. Sulfonamidyl radicals, generated through fragmentation of α-iodoaziridines, undergo initial addition to [1.1.1]propellane to afford iodo-BCPAs; the newly formed C–I bond in these products is then functionalized via a silyl-mediated Giese reaction. This chemistry also translates smoothly to 1,3-disubstituted iodo-BCPs. A wide variety of radical acceptors and iodo-BCPAs are accommodated, providing straightforward access to an array of valuable aniline-like isosteres.

中文翻译：

N,C-双官能化双环[1.1.1]戊烷的双重自由基合成

双环[1.1.1] pentylamines（BCPAs）是重要性日益增加，以制药业作为藻^3个苯胺和富含的bioisosters ñ -叔丁基的基团。在这里，我们报告了使用双重自由基功能化策略轻松合成 1,3-二取代 BCPA。磺胺基自由基，通过 α-碘氮丙啶的碎裂产生，经过初始添加到 [1.1.1] 丙烷中，得到碘-BCPA；然后通过甲硅烷基介导的 Giese 反应将这些产物中新形成的 C-I 键功能化。这种化学反应也可以顺利转化为 1,3-二取代碘-BCP。可容纳多种自由基受体和碘-BCPA，可直接获取一系列有价值的类苯胺等排体。

更新日期：2021-07-07

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