Frontiers in Chemistry (Oct 2022)

Redox-neutral and metal-free synthesis of 3-(arylmethyl)chroman-4-ones via visible-light-driven alkene acylarylation

  • Yan Ding,
  • Shengjiao Yu,
  • Man Ren,
  • Ji Lu,
  • Qiang Fu,
  • Zhijie Zhang,
  • Qin Wang,
  • Jun Bai,
  • Na Hao,
  • Lin Yang,
  • Siping Wei,
  • Dong Yi,
  • Jun Wei

DOI
https://doi.org/10.3389/fchem.2022.1059792
Journal volume & issue
Vol. 10

Abstract

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A metal- and aldehyde-free visible-light-driven photoredox-neutral alkene acylarylation with readily available cyanoarenes is described. A variety of 3-(arylmethyl)chroman-4-ones (i.e., homoisoflavonoids) and analogs are efficiently synthesized with good functional group tolerance. This mild protocol relies on a phosphoranyl radical-mediated acyl radical-initiated cyclization and selective radical-radical coupling sequence, and is also further highlighted by subsequent derivatization to chromone and 2H-chromene as well as its application in the three-component alkene acylarylation.

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