Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

Synthesis of Octaaryl Naphthalenes and Anthracenes with Different Substituents

Synthesis of Octaaryl Naphthalenes and Anthracenes with Different Substituents
Shin Suzuki, Kenichiro Itami, Junichiro Yamaguchi
A synthesis of multiply arylated naphthalenes and anthracenes with eight different substituents has been accomplished. The key intermediates are tetraarylthiophene S-oxides, which are synthesized through a method involving sequential C−H arylation and cross-coupling from 3-methoxythiophene, followed by oxidation of the sulfur atom. The resulting tetraarylthiophene S-oxides can be converted into a tetraaryl benzynes or naphthalynes and then merged through [4+2] cycloaddition reaction with another tetraarylthiophene S-oxide, thereby resulting in the programmed synthesis of octaarylnaphthalenes and octaarylanthracenes. Straight to eight: A novel method is presented that enables the synthesis of octaarylnaphthalenes (OANs) and octaarylanthracenes (OAAs) with eight different aryl substituents through [4+2] cycloaddition of tetraarylthiophene S-oxides with multiply arylated arynes.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201709332

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