Achieving C(sp2)–C(sp3) Coupling with BCP-F2 Building Blocks via Barluenga Coupling: A Comparative Approach,The Journal of Organic Chemistry

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Achieving C(sp2)–C(sp3) Coupling with BCP-F2 Building Blocks via Barluenga Coupling: A Comparative Approach
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-07-27 , DOI: 10.1021/acs.joc.1c01370
Xiaoshen Ma ₁ , Charles S Yeung ₁

Affiliation

We report our efforts toward achieving C(sp²)–C(sp³) coupling reactions with 2,2-difluorobicyclo[1.1.1]pentane (BCP-F₂) building blocks. By comparing the reactivities of matching pairs of bicyclo[1.1.1]pentane (BCP) and BCP-F₂ analogues, we discovered that the Barluenga coupling reaction was the only cross-coupling protocol that translated well between the two structural motifs in contrast to other reported protocols. In this chemistry, a BCP-F₂ bearing a tosylhydrazone functional group is cross-coupled with an arylboronic acid. These results further expanded the scope of BCP-F₂ building blocks for potential applications in organic chemistry as well as medicinal chemistry.

中文翻译：

通过 Barluenga 耦合实现 C(sp2)–C(sp3) 与 BCP-F2 构建块的耦合：一种比较方法

我们报告了我们为实现 C(sp ² )–C(sp ³ ) 偶联反应与 2,2-二氟双环[1.1.1] 戊烷 (BCP-F ₂ ) 构建单元所做的努力。通过比较双环 [1.1.1] 戊烷 (BCP) 和 BCP-F ₂类似物匹配对的反应性，我们发现 Barluenga 偶联反应是唯一一种在两种结构基序之间转换良好的交叉偶联方案，与其他报告的协议。在该化学中，带有甲苯磺酰腙官能团的 BCP-F ₂与芳基硼酸交叉偶联。这些结果进一步扩展了 BCP-F ₂构建块的范围，用于有机化学和药物化学的潜在应用。

更新日期：2021-08-07

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