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- Title
Gold‐Catalyzed Annulation of 1,8‐Dialkynylnaphthalenes: Synthesis and Photoelectric Properties of Indenophenalene‐Based Derivatives.
- Authors
Fard, Sara Tavakkoli; Sekine, Kohei; Farshadfar, Kaveh; Rominger, Frank; Rudolph, Matthias; Ariafard, Alireza; Hashmi, A. Stephen K.
- Abstract
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.
- Subjects
ANNULATION; GOLD catalysts; PHOTOELECTRIC effect; CATALYSIS; GOLD
- Publication
Chemistry - A European Journal, 2021, Vol 27, Issue 10, p3552
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202004846