A Pivotal Role of Chloride Ion on Nickel-Catalyzed Enantioselective Reductive Cross-Coupling to Perfluoroalkylated Boronate Esters,ACS Catalysis

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A Pivotal Role of Chloride Ion on Nickel-Catalyzed Enantioselective Reductive Cross-Coupling to Perfluoroalkylated Boronate Esters
ACS Catalysis ( IF 11.3 ) Pub Date : 2021-09-24 , DOI: 10.1021/acscatal.1c03265
Dong Wang ₁ , Tao XU ₁

Affiliation

The enantioselective construction of perfluoroalkyl-containing molecules is essential in materials science, agrochemistry, and medicinal chemistry. Herein, a nickel-catalyzed reductive cross-coupling was reported to generate chiral perfluoroalkylated boronate esters from the easily prepared perfluoroalkyl-substituted α-iodoboronates. The simple and mild conditions enable a broad range of aryl iodides to deliver the products in good enantioselectivities. Additionally, compared with common acceleration by iodide salts on substrate activation, the effect of the additive was systematically investigated to disclose a pivotal role of chloride ion on nickel reduction for this transformation.

中文翻译：

氯离子对镍催化对映选择性还原交叉偶联全氟烷基化硼酸酯的关键作用

含全氟烷基分子的对映选择性构建在材料科学、农业化学和药物化学中是必不可少的。在此，据报道，镍催化的还原交叉偶联可从易于制备的全氟烷基取代的 α-碘硼酸酯生成手性全氟烷基化硼酸酯。简单和温和的条件使广泛的芳基碘化物能够以良好的对映选择性提供产品。此外，与碘盐对底物活化的常见加速相比，系统研究了添加剂的影响，以揭示氯离子对镍还原的关键作用。

更新日期：2021-10-15

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