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Gold‐Catalyzed Annulation of 1,8‐Dialkynylnaphthalenes: Synthesis and Photoelectric Properties of Indenophenalene‐Based Derivatives
Author(s) -
Fard Sara Tavakkoli,
Sekine Kohei,
Farshadfar Kaveh,
Rominger Frank,
Rudolph Matthias,
Ariafard Alireza,
Hashmi A. Stephen K.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004846
Subject(s) - annulation , photoelectric effect , catalysis , chemistry , combinatorial chemistry , organic chemistry , materials science , optoelectronics
A simple gold‐catalyzed annulation of 1,8‐dialkynylnaphthalenes utilizing a cationic gold catalyst was developed. Such a peri ‐position of two alkynyl substituents has not been studied in gold catalysis before. Dependent on the substrate, the reactions either follow a mechanism involving vinyl cation intermediates or involve a dual gold catalysis mechanism which in an initial 6‐endo‐dig ‐cyclization generates gold(I) vinylidene intermediates that are able to insert into C−H bonds. Indenophenalene derivatives were obtained in moderate to high yields. In addition, the bidirectional gold‐catalyzed annulation of tetraynes provided even larger conjugated π‐systems. The optoelectronic properties of the products were also investigated.