Jump to main content
Jump to site search

Issue 12, 2014
Previous Article Next Article

Palladium catalyzed aryl C–H amination with O2via in situ formation of peroxide-based oxidant(s) from dioxane

Author affiliations

Abstract

(DAF)Pd(OAc)2 (DAF = 4,5-diazafluorenone) catalyzes aerobic intramolecular aryl C–H amination with N-benzenesulfonyl-2-aminobiphenyl in dioxane to afford the corresponding carbazole product. Mechanistic studies show that the reaction involves in situ generation of peroxide species from 1,4-dioxane and O2, and the reaction further benefits from the presence of glycolic acid, an oxidative decomposition product of dioxane. An induction period observed for the formation of the carbazole product correlates with the formation of 1,4-dioxan-2-hydroperoxide via autoxidation of 1,4-dioxane, and the in situ-generated peroxide is proposed to serve as the reactive oxidant in the reaction. These findings have important implications for palladium-catalyzed aerobic oxidation reactions conducted in ethereal solvents.

Graphical abstract: Palladium catalyzed aryl C–H amination with O2via in situ formation of peroxide-based oxidant(s) from dioxane

Back to tab navigation

Supplementary files

Publication details

The article was received on 11 Jun 2014, accepted on 01 Aug 2014 and first published on 01 Aug 2014


Article type: Paper
DOI: 10.1039/C4CY00764F
Author version available: Download Author version (PDF)
Citation: Catal. Sci. Technol., 2014,4, 4301-4307
  •   Request permissions

    Palladium catalyzed aryl C–H amination with O2via in situ formation of peroxide-based oxidant(s) from dioxane

    A. B. Weinstein and S. S. Stahl, Catal. Sci. Technol., 2014, 4, 4301
    DOI: 10.1039/C4CY00764F

Search articles by author

Spotlight

Advertisements