Symbiotic transition-metal and organocatalysis for catalytic ambient amine oxidation and alkene reduction reactions

Alexander T. Murray, Rose King, Joseph V. G. Donnelly, Myles J. H. Dowley, Floriana Tuna, Daniel Sells, Matthew P. John, David R. Carbery

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A new oxidation reaction based on two simple catalysts, namely, alloxan and a CuI salt, is highly effective for the aerobic oxidation and oxidative cross-coupling of amines. The reaction is operationally simple, reaction atmospheres enriched in dioxygen are obviated, and neither catalyst component requires prior synthesis. Mechanistic investigations have been performed and point towards a complex reaction manifold with evidence that supports a catalytic cycle that does not proceed through a quinone-imine step. Additionally, this dual catalyst system is efficient to effect diimide-mediated hydrogenation reactions of alkenes and alkynes, a transformation that has not been reported previously in the context of quinone catalyst systems.

Original languageEnglish
Pages (from-to)510-514
JournalChemCatChem
Volume8
Issue number3
Early online date22 Dec 2015
DOIs
Publication statusPublished - 5 Feb 2016

Fingerprint

Alkenes
alkenes
Olefins
Amines
Transition metals
amines
transition metals
Oxidation
oxidation
Catalysts
catalysts
quinones
alloxan
Alloxan
Imines
Alkynes
Hydrogenation
cross coupling
alkynes
Salts

Keywords

  • Amines
  • Copper
  • Cross-coupling
  • Homogeneous catalysis
  • Oxidation

Cite this

Symbiotic transition-metal and organocatalysis for catalytic ambient amine oxidation and alkene reduction reactions. / Murray, Alexander T.; King, Rose; Donnelly, Joseph V. G.; Dowley, Myles J. H.; Tuna, Floriana; Sells, Daniel; John, Matthew P.; Carbery, David R.

In: ChemCatChem, Vol. 8, No. 3, 05.02.2016, p. 510-514.

Research output: Contribution to journalArticle

Murray, Alexander T. ; King, Rose ; Donnelly, Joseph V. G. ; Dowley, Myles J. H. ; Tuna, Floriana ; Sells, Daniel ; John, Matthew P. ; Carbery, David R. / Symbiotic transition-metal and organocatalysis for catalytic ambient amine oxidation and alkene reduction reactions. In: ChemCatChem. 2016 ; Vol. 8, No. 3. pp. 510-514.
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