Iodine-Catalyzed Cascade Reaction of 2-Styrylbenzaldehydes with Indoles in the Synthesis of 1H-Indenes via 4π-Electrocyclization

Sundaram Suresh, Hao Yu Tsai, Xin Lun Han, Veerababurao Kavala, Sowndarya Palla, Ching Fa Yao*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A cascade reaction between 2-styrylbenzaldehydes and indoles has been developed for the synthesis of 1H-indenes. An iodine-catalyzed nucleophilic addition of indoles to an aldehyde group of 2-styrylbenzaldehydes leads to the formation of carbocation intermediates that undergo 4π-electrocyclization to give indenes with a trisubstituted double bond. These indenes are transformed into thermodynamically more stable products with a fully substituted double bond under the reaction conditions. Minor quantities of indolylbenzo[b]carbazoles are also produced as by-products.

Original languageEnglish
Pages (from-to)1436-1441
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume366
Issue number6
DOIs
Publication statusPublished - 2024 Mar 19

Keywords

  • 1H-Indene
  • 2-styrylbenzaldehydes
  • 4π-electrocyclization
  • indoles
  • indolylbenzo[b]carbazole

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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