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Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, molecular‐scale devices, organic light‐emitting diodes and candidates for organic electronics. Statistical synthesis of simple symmetrical HABs is known via cyclotrimerization or Diels–Alder reactions. By contrast, the synthesis of more complex, asymmetrical systems, and without involvement of statistical steps, remains an unsolved problem. Here we present a generally applicable synthetic strategy to access asymmetrical HAB via an atom‐economical and high‐yielding metal‐free four‐step domino reaction using nitrostyrenes and α,α‐dicyanoolefins as easily available starting materials. Resulting domino product—functionalized triarylbenzene (TAB)—can be used as a key starting compound to furnish asymmetrically substituted hexaarylbenzenes in high overall yield and without involvement of statistical steps. This straightforward domino process represents a distinct approach to create diverse and still unexplored HAB scaffolds, containing six different aromatic rings around central benzene core. [ABSTRACT FROM AUTHOR]

Aromatic system, domino reaction, functionalized triarylbenzene, hexaarylbenzene, non-statistical synthesis Titelbild: Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups (Angew. Keywords: aromatic system; domino reaction; functionalized triarylbenzene; hexaarylbenzene; non-statistical synthesis EN aromatic system domino reaction functionalized triarylbenzene hexaarylbenzene non-statistical synthesis 22257 22257 1 09/29/21 20211004 NES 211004 B Hexaarylbenzol-Grundgerüste b , die sechs verschiedene aromatische Ringe um einen zentralen Benzolkern enthalten, sind eine synthetische Herausforderung. [Extracted from the article]