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

Sara Tavakkoli Fard, Kohei Sekine, Kaveh Farshadfar, Frank Rominger, Matthias Rudolph, Alireza Ariafard, A. Stephen K. Hashmi

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)3552-3559
Number of pages8
JournalChemistry - A European Journal
Volume27
Issue number10
DOIs
Publication statusPublished - Feb 15 2021

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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