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Application of Primary Halogenated Hydrocarbons for the Synthesis of 3-Aryl and 3-Alkyl Indolizines

Abstract

Indolizine is an important heterocyclic compound with several interesting properties that make it suitable for numerous applications in many fields, such as biology, medicine and materials. However, the synthesis of 3-alkyl indolizines from bulky primary halogenated alkanes has not yet been reported. Herein, a transition-metal-free synthetic route to 3-aryl and 3-alkyl indolizines from electron-deficient alkenes, pyridines and primary halogenated hydrocarbons is reported for the first time using a tandem reaction. The key step of this method is the oxidative dehydrogenative aromatization of a tetrahydroindolizine intermediate with 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO) as the oxidant. The advantages of this protocol are its use of easily available and cheap starting materials, the transition-metal-free conditions and its ready scalability.

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Publication details

The article was received on 21 Apr 2017, accepted on 18 May 2017 and first published on 18 May 2017


Article type: Paper
DOI: 10.1039/C7OB00980A
Citation: Org. Biomol. Chem., 2017, Accepted Manuscript
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    Application of Primary Halogenated Hydrocarbons for the Synthesis of 3-Aryl and 3-Alkyl Indolizines

    Y. Liu, H. Hu, J. Zhou, W. Wang, Y. He and C. Wang, Org. Biomol. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7OB00980A

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