华东师范大学王威团队报道了不对称Sonogashira偶联催化对映选择性合成平面手性柱[5]芳烃。相关研究成果于2024年9月11日发表在《德国应用化学》。

作为一种具有吸引人的平面手性的新型大环，柱状[5]芳烃在过去几十年中引起了越来越多的研究兴趣，使其能够在多孔材料、分子机器和手性发光材料等不同领域得到广泛应用。然而，平面手性柱[5]芳烃对映选择性合成的催化方法仍然难以捉摸。

该文中，研究人员报告了一种通过不对称Sonogashira偶联，对映选择性合成平面手性柱[5]芳烃的新方法，该方法可以获得各种高度官能化的，具有优异对映选择性的平面手性柱[6]芳烃，包括均环和杂环芳烃。有吸引力的是，所得的平面手性柱[5]芳烃在许多领域（如手性发光材料）显示出巨大的广泛应用潜力。

该项工作不仅能够成功合成具有丰富结构和功能多样性的，平面手性柱[5]芳烃作为实际应用的关键构建块，而且丰富了有机合成化学中的不对称交叉偶联方法。

附：英文原文

Title: Catalytic Enantioselective Synthesis of Planar Chiral Pillar[5]arenes via Asymmetric Sonogashira Coupling

Author: Xiao-Hua Zhou, Xin Zhang, Yi-Ru Song, Xue Li, Lin-Tao Bao, Wei-Tao Xu, Xu-Qing Wang, Hai-Bo Yang, Wei Wang

Issue&Volume: 2024-09-11

Abstract: As a novel type of macrocycles with attractive planar chirality, pillar[5]arenes have gained increasing research interest over the past decades, enabling their widespread applications in diverse fields such as porous materials, molecular machines, and chiral luminescence materials. However, the catalytic methodology towards the enantioselective synthesis of planar chiral pillar[5]arenes remains elusive. Here we report a novel method for the enantioselective synthesis of planar chiral pillar[5]arenes via asymmetric Sonogashira coupling, giving access to a wide range of highly functionalized planar chiral pillar[5]arenes, including both homo- and hetero-rimmed ones, with excellent enantioselectivities. Attractively, the resultant planar chiral pillar[5]arenes show great potential for widespread use in many areas such as chiral luminescent materials. This work not only enables the successful synthesis of planar chiral pillar[5]arenes with abundant structural and functional diversity as key building blocks for practical applications but also enriches the asymmetric cross-coupling methodologies in organic synthetic chemistry.

DOI: 10.1002/anie.202415190

Source: https://onlinelibrary.wiley.com/doi/10.1002/anie.202415190