Selective vicinal diiodination of polycyclic aromatic hydrocarbons

Vicinally diiodinated polycyclic aromatic hydrocarbons (I2‐PAHs) are accessible from the corresponding diborylated B2‐PAHs through boron/iodine exchange. The B2‐PAHs have been prepared via twofold electrophilic borylatio
Vicinally diiodinated polycyclic aromatic hydrocarbons (I2‐PAHs) are accessible from the corresponding diborylated B2‐PAHs through boron/iodine exchange. The B2‐PAHs have been prepared via twofold electrophilic borylation reactions templated by a vicinally disilylated benzene. Our protocol is applicable to fluorenes, acenes, annulated acenes, oligoaryls, and even [5]helicene. Using B2‐naphthalene as the example, we have shown that the reaction scope can, in principle, be expanded to include the synthesis of vicinally dibrominated and dihydroxylated PAHs. The usefulness of the building blocks provided by our method in the field of optoelectronic materials was demonstrated by the successful conversion of I2‐fluoranthene to the analogous doubly alkynylated fluoranthene emitter.
show moreshow less

Export metadata

  • Export Bibtex
  • Export RIS

Additional Services

    Share in Twitter Search Google Scholar
Metadaten
Author:Tanja Kaehler, Alexandra John, Tao Jin, Michael Bolte, Hans‐Wolfram Lerner, Matthias Wagner
URN:urn:nbn:de:hebis:30:3-570400
DOI:http://dx.doi.org/10.1002/ejoc.202000954
ISSN:1099-0690
Parent Title (German):European Journal of Organic Chemistry
Publisher:Wiley-VCH Verl.
Place of publication:Weinheim
Document Type:Article
Language:English
Date of Publication (online):2020/08/19
Date of first Publication:2020/08/19
Publishing Institution:Universitätsbibliothek Johann Christian Senckenberg
Release Date:2020/12/08
Tag:Halogenation; Iodine; Polycyclic aromatic hydrocarbons; Synthetic methods
Volume:2020
Pagenumber:5
First Page:5847
Last Page:5851
HeBIS PPN:476950988
Institutes:Biochemie und Chemie
Dewey Decimal Classification:540 Chemie und zugeordnete Wissenschaften
Sammlungen:Universitätspublikationen
Licence (German):License LogoCreative Commons - Namensnennung-Nicht kommerziell - Keine Bearbeitung 4.0

$Rev: 11761 $