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Synthesis
DOI: 10.1055/a-2770-5374
Paper

One-pot Synthesis of Fluorescent Alkenylated Benzo[a]imidazo[2,1,5‑c,d]indolizine via Tandem Intramolecular direct C–H Bond Arylation Cyclization/Mizoroki–Heck Reaction

Authors

  • Masashi Yamashita

    1   Chemistry and Biomolecular Science, Gifu University, Gifu, Japan (Ringgold ID: RIN12785)

  • Fumitoshi Shibahara

    1   Chemistry and Biomolecular Science, Gifu University, Gifu, Japan (Ringgold ID: RIN12785)

Supported by: Japan Society for the Promotion of Science 20H02733,22K18332,24K01480
Supported by: the Koshiyama Science and Technology Foundation
Supported by: the Ogawa Science and Technology Foundation
Supported by: the Endo Saijiro Memorial Foundation for Science and Technology
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We developed a one-pot synthetic method combining stepwise direct C-H bond arylation cyclization and Mizoroki-Heck reaction for the efficient synthesis of benzo[a]imidazo[2,1,5‑c,d]indolizine fluorescent cores. This method has a broad substrate scope and applies to both electron-donating and electron-withdrawing styrene derivatives. Evaluation of the photophysical properties revealed that the benzoimidazoindolizine fluorophores synthesized by this method exhibited a red shift of up to 40 nm in absorption and fluorescence compared to previously reported biaryl-type compounds.



Publication History

Received: 17 November 2025

Accepted after revision: 10 December 2025

Accepted Manuscript online:
11 December 2025

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