Synthesis and characterization of hexaarylbenzenes with five or six different substituents enabled by programmed synthesis

Shin Suzuki, Yasutomo Segawa, Kenichiro Itami*, Junichiro Yamaguchi

*この研究の対応する著者

研究成果: Article査読

111 被引用数 (Scopus)

抄録

Since its discovery in 1825, benzene has served as one of the most used and indispensable building blocks of chemical compounds, ranging from pharmaceuticals and agrochemicals to plastics and those used in organic electronic devices. Benzene has six hydrogen atoms that can each be replaced by different substituents, which means that the structural diversity of benzene derivatives is intrinsically extraordinary. The number of possible substituted benzenes from n different substituents is (2n + 2n2 + 4n3 + 3n4 + n6)/12. However, owing to a lack of general synthetic methods for making multisubstituted benzenes, this potentially huge structural diversity has not been fully exploited. Here, we describe a programmed synthesis of hexaarylbenzenes using C-H activation, cross-coupling and [4+2] cycloaddition reactions. The present method allows for the isolation and structure-property characterization of hexaarylbenzenes with distinctive aryl substituents at all positions for the first time. Moreover, the established protocol can be applied to the synthesis of tetraarylnaphthalenes and pentaarylpyridines.

本文言語English
ページ(範囲)227-233
ページ数7
ジャーナルNature Chemistry
7
3
DOI
出版ステータスPublished - 2015 3月
外部発表はい

ASJC Scopus subject areas

  • 化学 (全般)
  • 化学工学(全般)

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