High-Yielding and Divergent Paradigm for the Synthesis of <i>D</i><sub>2<i>h</i></sub>‑Symmetric Octakis-Substituted Pentiptycenequinones

Published on 2017-03-20T21:49:28Z (GMT) by
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.

Cite this collection

Vadehra, Geeta

S.; Jiang, Xing; Dotson, Jordan J.; Chu, Gong M.; Garcia-Garibay, Miguel A. (2017): High-Yielding and Divergent Paradigm for the Synthesis

of D2h‑Symmetric

Octakis-Substituted Pentiptycenequinones. ACS Publications.

https://doi.org/10.1021/acs.orglett.7b00606

Retrieved: 17 31, Apr 26, 2017 (GMT)