10.1021/acs.orglett.7b00606.s001 Geeta S. Vadehra Geeta S. Vadehra Xing Jiang Xing Jiang Jordan J. Dotson Jordan J. Dotson Gong M. Chu Gong M. Chu Miguel A. Garcia-Garibay Miguel A. Garcia-Garibay High-Yielding and Divergent Paradigm for the Synthesis of <i>D</i><sub>2<i>h</i></sub>‑Symmetric Octakis-Substituted Pentiptycenequinones American Chemical Society 2017 Pentiptycenequinone building blocks communication Symmetric Pd substituent Octakis-Substituted organometallic compounds alkynyl variety polyaromatic framework materials applications High-Yielding Divergent Paradigm triphenylmethyl Synthesi methyl allyl heteroaryl synthese functionalized derivatives yield preparation aryl octakis-substituted pentiptycene derivatives paradigm 2017-03-20 21:49:27 Journal contribution https://acs.figshare.com/articles/journal_contribution/High-Yielding_and_Divergent_Paradigm_for_the_Synthesis_of_i_D_i_sub_2_i_h_i_sub_Symmetric_Octakis-Substituted_Pentiptycenequinones/4768216 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.