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Record number 533675
Title Rim-Differentiated C5-Symmetric Tiara-Pillar[5]arenes
Author(s) Guo, Minjie; Wang, Xuemei; Zhan, Caihong; Demay-Drouhard, Paul; Li, Wenjiao; Du, Ke; Olson, Mark A.; Zuilhof, Han; Sue, Andrew C.H.
Source Journal of the American Chemical Society 140 (2018)1. - ISSN 0002-7863 - p. 74 - 77.
DOI http://dx.doi.org/10.1021/jacs.7b10767
Department(s) Laboratory for Organic Chemistry
VLAG
Publication type Refereed Article in a scientific journal
Publication year 2018
Abstract The synthesis of "rim-differentiated" C5-symmetric pillar[5]arenes, whose two rims are decorated with different chemical functionalities, has remained a challenging task. This is due to the inherent statistical nature of the cyclization of 1,4-disubstituted alkoxybenzenes with different substituents, which leads to four constitutional isomers with only 1/16th being rim-differentiated. Herein, we report a "preoriented" synthetic protocol based on FeCl3-catalyzed cyclization of asymmetrically substituted 2,5-dialkoxybenzyl alcohols. This yields an unprecedented 55% selectivity of the C5-symmetric tiara-like pillar[5]arene isomer among four constitutional isomers. Based on this new method, a series of functionalizable tiara-pillar[5]arene derivatives with C5-symmetry was successfully synthesized, isolated, and fully characterized in the solid state.
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