7 research outputs found
Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups*
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 DielsâAlder 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 productâfunctionalized triarylbenzene (TAB)âcan 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. © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH Gmb
Metal-Free Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups
Hexaarylbenzene (HAB)
derivatives are versatile aromatic systems playing a significant role as
chromophores, liquid crystalline materials, molecular receptors, redox
materials, organic light-emitting diodes and photochemical switches. Statistical
synthesis of simple symmetrical HABs is known via low-yielding 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 â 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 creating diverse and still unexplored HAB scaffolds, containing six
different aromatic rings around central benzene core
Fourâstep domino reaction enables fully controlled nonâstatistical synthesis of hexaarylbenzene with six different aryl groups
Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, molecularâscale devices, organic lightâemitting diodes and candidates for organic electronics. Statistical synthesis of simple symmetrical HABs is known via cyclotrimerization or DielsâAlder 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 atomâeconomical and highâyielding metalâfree fourâstep domino reaction using nitrostyrenes and α,αâdicyanoolefins as easily available starting materials. Resulting domino productâfunctionalized triarylbenzene (TAB)âcan 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