Mechanistic Insights into the FeCl3-Catalyzed Oxidative Cross-Coupling of Phenols with 2-Aminonaphthalenes

Vlada Vershinin, Hagit Forkosh, Mor Ben-Lulu, Anna Libman, Doron Pappo

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

The selective FeCl3-catalyzed oxidative cross-coupling reaction between phenols and primary, secondary, and tertiary 2-aminonaphthalene derivatives was investigated. The generality of this scalable method provides a sustainable alternative for preparing N,O-biaryl compounds that are widely used as ligands and catalysts. Based on a comprehensive kinetic investigation, a catalytic cycle involving a ternary complex that binds to both the coupling partners and the oxidant during the key oxidative coupling step is postulated. Furthermore, the studies showed that the reaction is regulated by off-cycle acid-base and ligand exchange processes.

Original languageEnglish
Pages (from-to)79-90
Number of pages12
JournalJournal of Organic Chemistry
Volume86
Issue number1
DOIs
StatePublished - 1 Jan 2021

ASJC Scopus subject areas

  • Organic Chemistry

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