Gold‐Catalyzed Annulation of 1,8‐Dialkynylnaphthalenes: Synthesis and Photoelectric Properties of Indenophenalene‐Based Derivatives
| Autor: | Sara Tavakkoli Fard, Kaveh Farshadfar, A. Stephen K. Hashmi, Frank Rominger, Kohei Sekine, Matthias Rudolph, Alireza Ariafard |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Annulation
Full Paper 010405 organic chemistry Chemistry Organic Chemistry Cationic polymerization Substrate (chemistry) General Chemistry Photoelectric effect Conjugated system Full Papers 010402 general chemistry alkynes annulation 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences bidirectional synthesis extended π systems Vinyl cation dual gold catalysis Gold Catalysis | Hot Paper |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) |
| ISSN: | 1521-3765 0947-6539 |
| Popis: | 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. The 6‐endo‐cyclization of the first diyne unit (blue) with two alkynes in peri‐position induces a switch to a 5‐exo‐cyclization for the second peri‐diyne unit (red) in the fast modular synthesis of new extended π‐systems. |
| Databáze: | OpenAIRE |
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