Grau B, Dill M, Hampel F, Kahnt A, Jux N, Tsogoeva S (2021)
Publication Type: Journal article
Publication year: 2021
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 alpha,alpha-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.
APA:
Grau, B., Dill, M., Hampel, F., Kahnt, A., Jux, N., & Tsogoeva, S. (2021). Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups**. Angewandte Chemie International Edition. https://dx.doi.org/10.1002/anie.202104437
MLA:
Grau, Benedikt, et al. "Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups**." Angewandte Chemie International Edition (2021).
BibTeX: Download