ol7b00606_si_001.pdf (8.62 MB)
High-Yielding and Divergent Paradigm for the Synthesis of D2h‑Symmetric Octakis-Substituted Pentiptycenequinones
journal contribution
posted on 2017-03-20, 21:49 authored by Geeta
S. Vadehra, Xing Jiang, Jordan J. Dotson, Gong M. Chu, Miguel A. Garcia-GaribayWith
a rigid fused polyaromatic framework and a well-defined, highly
symmetric molecular geometry, pentiptycenes are appealing building
blocks for a variety of materials applications. Unfortunately, their
use has been limited by the lengthy syntheses of their functionalized
derivatives. This communication describes a highly efficient, brief,
divergent paradigm for the preparation of octakis-substituted pentiptycene
derivatives that starts with the preparation of an octakis(bromo)
compound, which can be used as a Pd(0)-catalyzed coupling partner
with suitable organometallic compounds to install a range of groups
in high yields at the peripheral 2,3,6,7,14,15,19,20 positions,
including methyl, allyl, vinyl, alkynyl, aryl, heteroaryl, and even
bulky 4-(triphenylmethyl)phenyl substituents.
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Pentiptycenequinonebuilding blockscommunicationSymmetricPdsubstituentOctakis-Substitutedorganometallic compoundsalkynylvarietypolyaromatic frameworkmaterials applicationsHigh-YieldingDivergent ParadigmtriphenylmethylSynthesimethylallylheteroarylsynthesefunctionalized derivativesyieldpreparationaryloctakis-substituted pentiptycene derivativesparadigm
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