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Gold-catalyzed annulation of 1,8-dialkynylnaphthalenes: synthesis and photoelectric properties of indenophenalene-based derivatives

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Fard, ST, Sekine, K, Farshadfar, K, Rominger, F, Rudolph, M, Ariafard, A ORCID: 0000-0003-2383-6380 and Hashmi, ASK 2021 , 'Gold-catalyzed annulation of 1,8-dialkynylnaphthalenes: synthesis and photoelectric properties of indenophenalene-based derivatives' , Chemistry - A European Journal, vol. 27, no. 10 , pp. 3552-3559 , doi: 10.1002/chem.202004846.

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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 Type: Article
Authors/Creators:Fard, ST and Sekine, K and Farshadfar, K and Rominger, F and Rudolph, M and Ariafard, A and Hashmi, ASK
Keywords: gold catalysis, DFT calculations, annulation
Journal or Publication Title: Chemistry - A European Journal
Publisher: Wiley-V C H Verlag Gmbh
ISSN: 0947-6539
DOI / ID Number: 10.1002/chem.202004846
Copyright Information:

© 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.

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