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<p>A direct C–H imidoylmethylation and subsequent oxidation/cyclization reaction of 2-arylbenzimidazoles with CF<sub>3</sub>-imidoyl sulfoxonium ylides via Rh(III)/Cu(II) relay catalysis has been developed. This reaction proceeded under mild conditions in an O<sub>2</sub> atmosphere to afford an array of CF<sub>3</sub>-decorated imidazo[2,1-<i>a</i>]isoquinolin-5-ones, where O<sub>2</sub> acts as the oxygen donor for carbonyl group formation. This transformation involved an unprecedented cascade process including Rh(III)-catalyzed C–H imidoylmethylation and Cu(II)-mediated oxidation followed by cyclization. Notably, antitumor activity study revealed that some synthetic products exhibit promising antiproliferative activity against several cancer cell lines.</p> Graphical abstract <p></p>

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Synthesis of imidazo[2,1-a]isoquinolin-5-ones via C–H imidoylmethylation/oxidation/cyclization cascade of 2-arylbenzimidazoles with CF3-imidoyl sulfoxonium ylides by Rh(III)/Cu(II) relay catalysis

  • 期刊论文

  • 发表日期：

    2025年12月19日

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  • Juting Liao,
  • Ruirui Zhai,
  • Yuming Zhang,
  • Junyu Xu,
  • Hongliang Wu,
  • Guiwei Yao,
  • Yuchao Luo,
  • Dulin Kong,
  • Shuojin Wang,
  • Xun Chen

摘要

A direct C–H imidoylmethylation and subsequent oxidation/cyclization reaction of 2-arylbenzimidazoles with CF3-imidoyl sulfoxonium ylides via Rh(III)/Cu(II) relay catalysis has been developed. This reaction proceeded under mild conditions in an O2 atmosphere to afford an array of CF3-decorated imidazo[2,1-a]isoquinolin-5-ones, where O2 acts as the oxygen donor for carbonyl group formation. This transformation involved an unprecedented cascade process including Rh(III)-catalyzed C–H imidoylmethylation and Cu(II)-mediated oxidation followed by cyclization. Notably, antitumor activity study revealed that some synthetic products exhibit promising antiproliferative activity against several cancer cell lines.

Graphical abstract