Gold-Catalyzed Annulation of 1,8-Dialkynylnaphthalenes: Synthesis and Photoelectric Properties of Indenophenalene-Based Derivatives |
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| Authors: | Sara Tavakkoli Fard Dr Kohei Sekine Dr Kaveh Farshadfar Dr Frank Rominger Dr Matthias Rudolph Dr Alireza Ariafard Prof Dr A Stephen K Hashmi |
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| Institution: | 1. Organisch-Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany;2. Department of Chemistry, Islamic Azad University, Central Tehran Branch, Poonak, Tehran, 1469669191 Iran;3. School of Physical Sciences, University of Tasmania, Private Bag 75, Hobart, TAS, 7001 Australia |
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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. |
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| Keywords: | alkynes annulation bidirectional synthesis dual gold catalysis extended π systems |
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