TfOH-promoted Classical Nazarov-type Cyclization of Benzofulvenes: Synthesis of Polycyclic 5 H,10′ H-spiro[benzo[ k]phenanthridine-5,6′-dibenzopentalenes]

Shang You Sun, Selvam Raju, Guganchandar Vedarethinam, Pei Lin Chen, Shih Ching Chuang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

The reaction of o-benzofulvene with TfOH leads to intramolecular cyclization through novel C-C and C-N bond formation, resulting in the formation of 5H,10′H-spiro[benzo[k]phenanthridine-5,6′-dibenzopentalene]. This protocol provides a new molecular framework with reasonable to excellent yields and tolerates various electron-withdrawing/donating substituents. This method yields diastereoselectivity of up to >20:1. Furthermore, it is free of bases, oxidants, and metals and proceeds under mild reaction conditions, which are favorable for synthetic organic chemistry.

Original languageEnglish
Pages (from-to)6212-6216
Number of pages5
JournalOrganic Letters
Volume23
Issue number16
DOIs
StatePublished - 20 Aug 2021

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