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May 31, 2026The Journal of Organic Chemistry0 citations

Visible-Light-Driven Reductive 1,2-Diarylation of Alkenes via O -Tethered Iodoarenes and Cyanopyridines

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QLQing-Lin LiangPWPeiyuan WangYLY Li

Key Points

  • To develop an efficient method for alkene diarylation using visible-light-driven photoredox catalysis.
  • Developed a photoredox cascade approach using O-tethered iodoarenes.
  • Coupled alkenes with 4-cyanopyridines under visible light irradiation.
  • Utilized cyanopyridines as both a coupling partner and electron-transfer mediator.
  • Achieved successful diarylation of alkenes with broad functional group compatibility.
  • Produced diverse dihydrobenzofuran derivatives efficiently.
  • Facilitated cleavage of aryl C(sp2)–I bonds effectively with visible-light irradiation.

Abstract

The diarylation of alkenes represents one of the most efficient strategies for constructing complex architectures. Reported herein is a distinct photoredox cascade approach for alkene diarylation, achieved via the radical cyclization of O-tethered iodoarenes followed by coupling with 4-cyanopyridines. Notably, this protocol relies on the dual role of the cyanoheteroarenes. Beyond serving as the requisite heteroaryl source, they act as essential electron-transfer mediators to facilitate the cleavage of aryl C(sp2)–I bonds under visible-light irradiation. Furthermore, this photochemical strategy features readily accessible substrates and broad functional group compatibility, providing a practical platform for the efficient synthesis of diverse dihydrobenzofuran derivatives.

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Cite This Study

Liang et al. (2026) studied this question.

synapsesocial.com/papers/6a1bcfb05783ba022b6fbaa5https://doi.org/10.1021/acs.joc.6c00933
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