Metallaphotoredox-Catalyzed Three-Component Asymmetric Cross-Electrophile Coupling for Chiral Boronate Synthesis

IF 13.1 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2024-10-09 DOI:10.1021/acscatal.4c0431610.1021/acscatal.4c04316

Xiaofang Li, Yuntong Hu, Zhonghou Huang, Shengqing Zhu, Feng-Ling Qing and Lingling Chu*,

引用次数: 0

Abstract

Here, we report a photoredox and nickel-catalyzed cross-electrophile coupling strategy for the asymmetric three-component 1,2-alkylarylation of vinyl boronates with (hetero)aryl bromides and (2°, 3°)-alkyl redox-active esters in the presence of Hantzsch ester. With a fluorinated pyridyl-substituted chiral biimidazoline ligand, this reaction enables straightforward access to a wide variety of synthetically valuable chiral α-aryl boronates from readily available starting materials. This reaction features mild conditions, broad substrate generality, and good functional group tolerance and proceeds without using metal reductants or alkyl halides. Furthermore, alkenyl halides and other electron-deficient alkenes such as acrylates and vinyl phosphonates can be applied successfully. Preliminary mechanistic studies shed light on the potential reaction pathways and roles of organic amines.

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金属光氧催化三组分不对称交叉亲电偶联用于手性硼酸酯合成

在此，我们报告了一种光氧化和镍催化的交叉亲电偶联策略，用于在汉茨赫酯存在下，乙烯基硼酸盐与（杂）芳基溴化物和（2°, 3°）-烷基氧化还原活性酯的不对称三组份 1,2- 烷基芳基化反应。通过使用氟化吡啶基取代的手性双咪唑啉配体，该反应可从容易获得的起始材料中直接获得各种有合成价值的手性 α 芳基硼酸盐。该反应的特点是条件温和、底物通用性广、官能团耐受性好，并且无需使用金属还原剂或烷基卤化物。此外，烯基卤化物和其他缺电子烯类（如丙烯酸酯和乙烯基膦酸酯）也能成功应用。初步的机理研究揭示了有机胺的潜在反应途径和作用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.