High-Yielding and Divergent Paradigm for the Synthesis of D2h-Symmetric Octakis-Substituted Pentiptycenequinones.
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.
Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
Geeta S
GS
Vadehra
Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
Xing
0000-0001-8259-1948
X
Jiang
Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
Jordan J
JJ
Dotson
Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
Gong M
GM
Chu
Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
Miguel A
0000-0002-6268-1943
MA
Garcia-Garibay