Aryl Chloride-Directed Enantioselective C(sp2)-H Borylation Enabled by Iridium Catalysis,Journal of the American Chemical Society

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Aryl Chloride-Directed Enantioselective C(sp2)-H Borylation Enabled by Iridium Catalysis
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2023-11-07 , DOI: 10.1021/jacs.3c08129
Hongliang Zhao _{1,

2} , Chao-Yue Zhao ₃ , Lili Chen ₁ , Chungu Xia _{1,

2} , Xin Hong ₄ , Senmiao Xu _{1,

2,

5}

Affiliation

We herein report the iridium-catalyzed enantioselective C–H borylation of aryl chlorides. A variety of prochiral biaryl compounds could be well-tolerated, affording a vast array of axially chiral biaryls with high enantioselectivities. The current method exhibits a high turnover number (TON) of 7000, which represents the highest in functional-group-directed asymmetric C–H activation. The high TON was attributed to a weak catalyst-substrate interaction that was caused by mismatched chirality between catalyst and substrate. We also demonstrated the synthetic application of the current method by C–B, ortho-C–H, and C–Cl bond functionalization, including programmed Suzuki–Miyaura coupling for the synthesis of axially chiral polyarenes.

中文翻译：

铱催化实现芳基氯定向对映选择性 C(sp2)-H 硼化

我们在此报道了铱催化的芳基氯的对映选择性 C-H 硼基化反应。多种前手性联芳基化合物具有良好的耐受性，提供了大量具有高对映选择性的轴向手性联芳基化合物。目前的方法表现出 7000 的高转换数 (TON)，这代表了官能团定向的不对称 C-H 激活中的最高值。高 TON 归因于催化剂与底物之间的手性不匹配导致的弱催化剂-底物相互作用。我们还展示了当前方法通过 C-B、邻位C-H 和 C-Cl 键功能化的合成应用，包括用于合成轴向手性聚芳烃的程序化 Suzuki-Miyaura 偶联。

更新日期：2023-11-07

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