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

研究成果: Contribution to journalArticle査読

抄録

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.

本文言語英語
ページ(範囲)3552-3559
ページ数8
ジャーナルChemistry - A European Journal
27
10
DOI
出版ステータス出版済み - 2 15 2021

All Science Journal Classification (ASJC) codes

  • 触媒
  • 有機化学

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