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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
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
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