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.