Enantioselective construction of inherently chiral pillar[5]arenes via palladium-catalysed Suzuki–Miyaura cross-coupling

Ting-Rui Luan, Che Sun, Yong-Le Tian, Yu-Kun Jiang, Long-Long Xi () and Ren-Rong Liu ()
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Ting-Rui Luan: Qingdao University
Che Sun: Qingdao University
Yong-Le Tian: Qingdao University
Yu-Kun Jiang: Qingdao University
Long-Long Xi: Qingdao University
Ren-Rong Liu: Qingdao University

Nature Communications, 2025, vol. 16, issue 1, 1-12

Abstract: Abstract Pillar[n]arenes have broad applications in biological medicine, materials science, and supramolecular gels. Notably, enantiopure pillar[5]arenes are valued for their roles in enantioselective host–guest recognition, chiral sensing, asymmetric catalysis, and related fields. Current methods for obtaining chiral pillar[n]arenes rely heavily on resolution agents or chiral HPLC resolution. However, the synthesis of these compounds via asymmetric catalysis remains challenging. In this study, we develop an asymmetric extended side-arm Suzuki–Miyaura cross-coupling strategy to construct inherently chiral pillar[5]arenes with excellent yields and high enantioselectivities using a palladium catalyst and a Sadphos ligand. The reaction scope extends beyond arylboronic acids to encompass 2-arylvinylboronic acids and other multi-OTf-substituted substrates, all efficiently producing the desired products. Further exploration of the synthetic applications, along with photophysical and chiroptical analyses, confirm the potential of these chiral pillar[5]arenes for diverse applications across multiple disciplines.

Date: 2025
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DOI: 10.1038/s41467-025-57461-x

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