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High-Yielding and Divergent Paradigm for the Synthesis of D2h‑Symmetric Octakis-Substituted Pentiptycenequinones

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posted on 20.03.2017, 21:49 by Geeta S. Vadehra, Xing Jiang, Jordan J. Dotson, Gong M. Chu, Miguel A. Garcia-Garibay
With 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.