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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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Copyright Statement
© 2020 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) License, (https://creativecommons.org/licenses/by-nc-nd/4.0/) which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
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 |
|---|---|
| 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) |
| Web of Science® Times Cited: | 2 |
| Deposited By: | College Office - CoSE |
| Deposited On: | 2022-05-16 |
| Last Modified: | 2022-08-19 |
| Downloads: | 5 View Download Statistics |
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