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Selective Vicinal Diiodination of Polycyclic Aromatic Hydrocarbons
Author(s) -
Kaehler Tanja,
John Alexandra,
Jin Tao,
Bolte Michael,
Lerner HansWolfram,
Wagner Matthias
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000954
Subject(s) - fluoranthene , chemistry , naphthalene , helicene , borylation , polycyclic aromatic hydrocarbon , benzene , pyrene , vicinal , electrophile , boron , organic chemistry , computational chemistry , molecule , catalysis , alkyl , aryl
Vicinally diiodinated polycyclic aromatic hydrocarbons (I 2 ‐PAHs) are accessible from the corresponding diborylated B 2 ‐PAHs through boron/iodine exchange. The B 2 ‐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 B 2 ‐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 I 2 ‐fluoranthene to the analogous doubly alkynylated fluoranthene emitter.