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Gold-catalyzed annulation of 1,8-dialkynylnaphthalenes: synthesis and photoelectric properties of indenophenalene-based derivatives
Citation
Fard, ST and Sekine, K and Farshadfar, K and Rominger, F and Rudolph, M and Ariafard, A and Hashmi, ASK, Gold-catalyzed annulation of 1,8-dialkynylnaphthalenes: synthesis and photoelectric properties of indenophenalene-based derivatives, Chemistry - A European Journal, 27, (10) pp. 3552-3559. ISSN 0947-6539 (2021) [Refereed Article]
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DOI: doi:10.1002/chem.202004846
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.
Item Details
Item Type: | Refereed Article |
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Keywords: | gold catalysis, DFT calculations, annulation |
Research Division: | Chemical Sciences |
Research Group: | Physical chemistry |
Research Field: | Catalysis and mechanisms of reactions |
Objective Division: | Expanding Knowledge |
Objective Group: | Expanding knowledge |
Objective Field: | Expanding knowledge in the chemical sciences |
UTAS Author: | Ariafard, A (Associate Professor Alireza Ariafard) |
ID Code: | 150049 |
Year Published: | 2021 |
Funding Support: | Australian Research Council (DP180100904) |
Deposited By: | College Office - CoSE |
Deposited On: | 2022-05-16 |
Last Modified: | 2022-05-18 |
Downloads: | 0 |
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