Chemistry - A European Journal p. 3552 - 3559 (2021)
Update date:2022-08-04
Topics:
Fard, Sara Tavakkoli
Sekine, Kohei
Farshadfar, Kaveh
Rominger, Frank
Rudolph, Matthias
Ariafard, Alireza
Hashmi, A. Stephen K.
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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