<i>ortho</i>-Functionalization of Pillar[5]arene: An Approach to Mono-<i>ortho</i>-Alkyl/Aryl-Substituted A1/A2-Dihydroxypillar[5]arene
Zhuo Wang, Yahu A. Liu, Hui Yang, Wei‐Bo Hu, Ke Wen
Abstract
Despite the fact that the rim and lateral functionalizations of pillar[n]arenes have been well explored, ortho-functionalization has rarely been realized. In this work, we report a facile method of introducing a single functionality ortho to the hydroxyl group in A1/A2-dihydroxypillar[5]arene via a Grignard addition to pillar[4]arene[1]quinone followed by a dienone–phenol rearrangement. The described ortho-alkylation/arylation method allowed formation of various mono ortho-alkyl/aryl-substituted A1/A2-dihydroxypillar[5]arenes previously difficult to obtain.
Topics & Concepts
ChemistryAlkylPillarArylSurface modificationAlkylationPhenolQuinoneStereochemistryMedicinal chemistryCombinatorial chemistryOrganic chemistryCatalysisStructural engineeringEngineeringPhysical chemistrySupramolecular Chemistry and ComplexesMolecular spectroscopy and chiralityAdvanced NMR Techniques and Applications