Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups*.
aromatic system
domino reaction
functionalized triarylbenzene
hexaarylbenzene
non-statistical synthesis
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
04 Oct 2021
04 Oct 2021
Historique:
revised:
30
05
2021
received:
30
03
2021
pubmed:
2
6
2021
medline:
2
6
2021
entrez:
1
6
2021
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 34060211
doi: 10.1002/anie.202104437
pmc: PMC8518863
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
22307-22314Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : TS87/17-1
Organisme : Deutsche Forschungsgemeinschaft
ID : TS87/23-1
Organisme : Deutsche Forschungsgemeinschaft
ID : SFB953, grant Nr. 182849149
Organisme : Solar Technologies go Hybrid
Informations de copyright
© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
Références
J Am Chem Soc. 2010 Sep 29;132(38):13223-5
pubmed: 20815344
Chem Rev. 2007 Mar;107(3):718-47
pubmed: 17291049
Bioorg Chem. 2019 Mar;84:276-284
pubmed: 30529845
Phys Chem Chem Phys. 2020 May 28;22(20):11529-11536
pubmed: 32393952
Angew Chem Int Ed Engl. 2021 Oct 4;60(41):22307-22314
pubmed: 34060211
J Am Chem Soc. 2019 Jan 9;141(1):3-10
pubmed: 30395456
Angew Chem Int Ed Engl. 2016 Apr 25;55(18):5602-5
pubmed: 27010964
J Phys Chem Lett. 2016 Mar 3;7(5):783-8
pubmed: 26882341
Org Lett. 2014 Feb 7;16(3):1024-7
pubmed: 24450929
Chem Sci. 2019 Jun 5;10(27):6642-6650
pubmed: 31367317
J Am Chem Soc. 2019 Oct 2;141(39):15649-15655
pubmed: 31491075
Chemistry. 2016 Apr 4;22(15):5189-97
pubmed: 26919489
Angew Chem Int Ed Engl. 2012 Jul 27;51(31):7640-54
pubmed: 22777811
Nat Chem. 2015 Mar;7(3):227-33
pubmed: 25698332
Angew Chem Int Ed Engl. 2006 Nov 6;45(43):7134-86
pubmed: 17075967
Chemistry. 2018 May 2;24(25):6551-6556
pubmed: 29325200
J Org Chem. 2007 Jul 6;72(14):5443-5
pubmed: 17567078
J Org Chem. 2019 Feb 1;84(3):1489-1499
pubmed: 30596243
J Med Chem. 2014 Jul 24;57(14):5845-59
pubmed: 24471928
Chem Commun (Camb). 2013 May 25;49(42):4827-9
pubmed: 23595595
Chem Soc Rev. 2015 Sep 21;44(18):6616-43
pubmed: 26186682
Nat Commun. 2017 May 02;8:15071
pubmed: 28462939
Angew Chem Int Ed Engl. 2005 Dec 1;44(45):7337-9
pubmed: 16206312
Chem Rev. 2016 Aug 24;116(16):9565-627
pubmed: 27498592
Top Curr Chem (Cham). 2019 Oct 25;377(6):31
pubmed: 31654245