The Trouble with Five: New Synthetic Strategies toward C5-Symmetric Pillar[5]arenes and Beyond

Ke Du; Andrew C.-H. Sue

doi:10.1055/s-0037-1611921

Synlett, Table of Contents

Synlett 2019; 30(20): 2209-2215
DOI: 10.1055/s-0037-1611921

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The Trouble with Five: New Synthetic Strategies toward C₅ -Symmetric Pillar[5]arenes and Beyond

Ke Du

,

Andrew C.-H. Sue ∗

Institute for Molecular Design and Synthesis, School of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Rd., Nankai Dist., Tianjin 300072, P. R. of China Email: andrew.sue@tju.edu.cn

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Abstract

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Abstract

Rim-differentiated pillar[5]arenes (P[5]s) are intriguing macrocyclic molecular platforms with C ₅-symmetry, but their conventional statistical syntheses suffer from low yields and laborious separation. Our group recently reported a ‘pre-oriented’ protocol that results in highly selective production of C ₅-symmetric P[5]s among four constitutional isomers. Subsequently, we devised a more general divergent synthetic route starting with a common P[5] precursor with rim differentiation, followed by a series of high-yielding reactions that permit successive transformations of both rims freely. As a result, a variety of rim-differentiated P[5]s can be made to order in gram-scale quantities. This total solution not only populates the list of C ₅-symmetric P[5]s, but also enables further design and synthesis of assorted five-fold organic building blocks towards complex supramolecular architectures.

Key words

five-fold symmetry - C ₅-axis - pillar[5]arenes - rim differentiation - regioselectivity - macrocycles

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References

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The Trouble with Five: New Synthetic Strategies toward C5 -Symmetric Pillar[5]arenes and Beyond

The Trouble with Five: New Synthetic Strategies toward C₅ -Symmetric Pillar[5]arenes and Beyond