FeCl3-Catalyzed Oxidative Allylation of sp2 and sp3 C−H Bond Adjacent to a Nitrogen Atom: Easy Access to Homoallyl Tertiary Amines

FeCl3-Catalyzed Oxidative Allylation of sp2 and sp3 C−H Bond Adjacent to a Nitrogen Atom: Easy Access to Homoallyl Tertiary Amines

Oxidative allylation to sp2- and sp3-carbon attached to the nitrogen atom was accomplished. The α-allylation of tertiary amines was catalyzed by easily available hydrated iron(III) chloride in combination with air or aqueous tBuOOH. Remarkably, N-allyl- and N-propagyl-tethered tertiary amines were a...

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Veröffentlicht in:Journal of organic chemistry 2010-06, Vol.75 (11), p.3916-3919
Hauptverfasser: Kumaraswamy, Gullapalli, Murthy, Akula Narayana, Pitchaiah, Arigala
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Kinetics and mechanisms
Organic chemistry
Preparations and properties
Reactivity and mechanisms
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Zusammenfassung:Oxidative allylation to sp2- and sp3-carbon attached to the nitrogen atom was accomplished. The α-allylation of tertiary amines was catalyzed by easily available hydrated iron(III) chloride in combination with air or aqueous tBuOOH. Remarkably, N-allyl- and N-propagyl-tethered tertiary amines were also allylated through this protocol.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo1005813