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Updated: Jun 4, 2025
Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Photocatalytic Alkene-Migrative Chain Elongation of 2-Phosphinostyrenes with Aldehydes
Haruna Mori1, Ayaka Sakurada1, Masaya Sawamura1,2
1Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan.
Abstract:
The photocatalytic alkene-migrative chain elongation reaction of 2-phosphinostyrenes with aldehydes under mild conditions in response to blue light was demonstrated. A broad range of aldehydes, both aliphatic and aromatic, participated in this reaction to afford alkene-phosphine oxides in a Z-selective manner. Mechanistic experiments suggested the formation of benzophospholene-based ylide intermediates via photocatalytic cyclization of phosphinostyrenes followed by solvent-mediated proton transfer under base-free reaction conditions.
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