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Gold-Catalyzed Annulation of 1,8-Dialkynylnaphthalenes: Synthesis and Photoelectric Properties of Indenophenalene-Based Derivatives.

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 ?-systems. The optoelectronic properties of the products were also investigated.

SUBMITTER: Fard ST 

PROVIDER: S-EPMC7898384 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Gold-Catalyzed Annulation of 1,8-Dialkynylnaphthalenes: Synthesis and Photoelectric Properties of Indenophenalene-Based Derivatives.

Fard Sara Tavakkoli ST   Sekine Kohei K   Farshadfar Kaveh K   Rominger Frank F   Rudolph Matthias M   Ariafard Alireza A   Hashmi A Stephen K ASK  

Chemistry (Weinheim an der Bergstrasse, Germany) 20210119 10

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  ...[more]

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