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150049 - Gold-catalyzed annulation of 1 8-dialkynylnaphthalenes.pdf (1.74 MB)

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

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posted on 2023-05-21, 07:38 authored by Fard, ST, Sekine, K, Farshadfar, K, Rominger, F, Rudolph, M, Alireza AriafardAlireza Ariafard, Hashmi, ASK

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.

Funding

Australian Research Council

University of Wollongong

History

Publication title

Chemistry - A European Journal

Volume

27

Issue

10

Pagination

3552-3559

ISSN

0947-6539

Department/School

College Office - College of Sciences and Engineering

Publisher

Wiley-V C H Verlag Gmbh

Place of publication

Po Box 10 11 61, Weinheim, Germany, D-69451

Rights 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.

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  • Open

Socio-economic Objectives

Expanding knowledge in the chemical sciences

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