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

被引:0
|
作者
Luan, Ting-Rui [1 ]
Sun, Che [1 ]
Tian, Yong-Le [1 ]
Jiang, Yu-Kun [1 ]
Xi, Long-Long [1 ]
Liu, Ren-Rong [1 ,2 ]
机构
[1] Qingdao Univ, Coll Chem & Chem Engn, Qingdao, Peoples R China
[2] Guizhou Univ, Coll Pharmaceut Sci, Guiyang, Guizhou, Peoples R China
基金
中国国家自然科学基金;
关键词
ASYMMETRIC-SYNTHESIS; INVERSION; LIGANDS; ATROPISOMERS; CHEMISTRY; ARYLATION;
D O I
10.1038/s41467-025-57461-x
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
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.
引用
收藏
页数:12
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