Photocatalytic\nAlkene-Migrative Chain Elongation of\n2‑Phosphinostyrenes with Aldehydes

The photocatalytic alkene-migrative chain elongation\nreaction of\n2-phosphinostyrenes with aldehydes under mild conditions in response\nto blue light was demonstrated. A broad range of aldehydes, both aliphatic\nand aromatic, participated in this reaction to afford alkene-phosphine\noxides in a <i>Z</i>-selective manner. Mechanistic experiments\nsuggested the formation of benzophospholene-based ylide intermediates\nvia photocatalytic cyclization of phosphinostyrenes followed by solvent-mediated\nproton transfer under base-free reaction conditions.

Publication Details

Journal
Figshare
Published
2024-12-28
DOI
https://doi.org/10.1021/acs.orglett.4c04424.s001
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Photocatalytic\nAlkene-Migrative Chain Elongation of\n2‑Phosphinostyrenes with Aldehydes

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Radical Photochemical Reactions
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Photocatalytic\nAlkene-Migrative Chain Elongation of\n2‑Phosphinostyrenes with Aldehydes

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Abstract

The photocatalytic alkene-migrative chain elongation\nreaction of\n2-phosphinostyrenes with aldehydes under mild conditions in response\nto blue light was demonstrated. A broad range of aldehydes, both aliphatic\nand aromatic, participated in this reaction to afford alkene-phosphine\noxides in a <i>Z</i>-selective manner. Mechanistic experiments\nsuggested the formation of benzophospholene-based ylide intermediates\nvia photocatalytic cyclization of phosphinostyrenes followed by solvent-mediated\nproton transfer under base-free reaction conditions.

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Radical Photochemical Reactions
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Photocatalytic\nAlkene-Migrative Chain Elongation of\n2‑Phosphinostyrenes with Aldehydes · Figshare (2024) | TGRS Research Map | TGRS