Palladium-Catalyzed Oxidative Cyclization for the Synthesis of 2-Alkylimidazo[5,1,2-cd]indolizines

Sanjay Kumar Ghosh, Debalina Ghosh, Ratnava Maitra, Ya Ting Kuo, Hon Man Lee

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

An effective palladium-catalyzed direct arylation of 2-alkyl-imidazo[1,2-a]pyridine with alkynes towards imidazo[5,1,2-cd]indolizines through double C–H functionalization was developed. The catalyst system is an ionic palladium(II) complex bearing amido-functionalized N-heterocyclic carbene and triphenylphosphine ligands. A mere 2.5 mol-% loading of palladium was sufficient for catalyzing the reactions. Copper acetate and n-tetrabutylammonium bromide were employed as oxidant and phase-transfer catalyst, respectively. Beside imidazo[1,2-a]pyridine, desirably, less electron-rich derivatives could be employed as coupling partners. Also a wide range of diarylalkynes was used. The structure of one 2-alkyl-imidazo[5,1,2-cd]indolizine was established by single-crystal X-ray diffraction analysis. UV and PL spectra of the compounds confirmed that some are highly fluorescent. The method provides an easy synthetic route for the preparation of these new fluorescent materials.

Original languageEnglish
Pages (from-to)5722-5731
Number of pages10
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number34
DOIs
Publication statusPublished - 2016 Jan 1

Fingerprint

Indolizines
Cyclization
Palladium
palladium
pyridines
Bearings (structural)
synthesis
catalysts
Catalysts
Alkynes
carbenes
alkynes
Oxidants
X ray diffraction analysis
bromides
Copper
acetates
Acetates
routes
Single crystals

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Ghosh, Sanjay Kumar ; Ghosh, Debalina ; Maitra, Ratnava ; Kuo, Ya Ting ; Lee, Hon Man. / Palladium-Catalyzed Oxidative Cyclization for the Synthesis of 2-Alkylimidazo[5,1,2-cd]indolizines. In: European Journal of Organic Chemistry. 2016 ; Vol. 2016, No. 34. pp. 5722-5731.
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Palladium-Catalyzed Oxidative Cyclization for the Synthesis of 2-Alkylimidazo[5,1,2-cd]indolizines. / Ghosh, Sanjay Kumar; Ghosh, Debalina; Maitra, Ratnava; Kuo, Ya Ting; Lee, Hon Man.

In: European Journal of Organic Chemistry, Vol. 2016, No. 34, 01.01.2016, p. 5722-5731.

Research output: Contribution to journalArticle

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