Palladium-catalyzed direct synthesis of carbazoles via one-pot N-arylation and oxidative biaryl coupling: synthesis and mechanistic study

Toshiaki Watanabe; Shinya Oishi; Nobutaka Fujii; Hiroaki Ohno

doi:10.1021/jo9003376

Palladium-catalyzed direct synthesis of carbazoles via one-pot N-arylation and oxidative biaryl coupling: synthesis and mechanistic study

J Org Chem. 2009 Jul 3;74(13):4720-6. doi: 10.1021/jo9003376.

Authors

Toshiaki Watanabe¹, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.

PMID: 19489575
DOI: 10.1021/jo9003376

Abstract

An efficient catalytic system has been developed for the synthesis of carbazoles by one-pot N-arylation and oxidative biaryl coupling. A significant substituent effect of the diarylamine intermediate on oxidative coupling was observed. Mechanistic studies of oxidative coupling, including trapping of reaction intermediates and kinetic isotope effect experiments, are also presented.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbazoles / chemical synthesis*
Carbazoles / chemistry
Catalysis
Molecular Structure
Oxidation-Reduction
Palladium / chemistry*
Structure-Activity Relationship

Substances

Carbazoles
Palladium