Copper-Catalyzed Cross-Coupling of Benzylic C–H Bonds and Azoles with Controlled N-Site Selectivity,Journal of the American Chemical Society

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Copper-Catalyzed Cross-Coupling of Benzylic C–H Bonds and Azoles with Controlled N-Site Selectivity
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2021-08-31 , DOI: 10.1021/jacs.1c07117
Si-Jie Chen ₁ , Dung L Golden ₁ , Shane W Krska ₂ , Shannon S Stahl ₁

Affiliation

Azoles are important motifs in medicinal chemistry, and elaboration of their structures via direct N–H/C–H coupling could have broad utility in drug discovery. The ambident reactivity of many azoles, however, presents significant selectivity challenges. Here, we report a copper-catalyzed method that achieves site-selective cross-coupling of pyrazoles and other N–H heterocycles with substrates bearing (hetero)benzylic C–H bonds. Excellent N-site selectivity is achieved, with the preferred site controlled by the identity of co-catalytic additives. This cross-coupling strategy features broad scope for both the N–H heterocycle and benzylic C–H coupling partners, enabling application of this method to complex molecule synthesis and medicinal chemistry.

中文翻译：

铜催化的苄基 C-H 键和唑类的交叉偶联，具有受控的 N 位选择性

唑类是药物化学中的重要基序，通过直接 N-H/C-H 偶联来阐述其结构可能在药物发现中具有广泛的用途。然而，许多唑类的环境反应性提出了重大的选择性挑战。在这里，我们报道了一种铜催化方法，该方法实现了吡唑和其他 N-H 杂环与带有（杂）苄基 C-H 键的底物的位点选择性交叉偶联。实现了优异的N位点选择性，优选位点由助催化添加剂的特性控制。这种交叉偶联策略具有广泛的 N-H 杂环和苄基 C-H 偶联伙伴的范围，使得该方法能够应用于复杂的分子合成和药物化学。

更新日期：2021-09-15

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