Photochemical Homologation for the Preparation of Aliphatic Aldehydes in Flow

Yiding Chen, Marco Leonardi, Paul Dingwall, Ricardo Labes, Patrick Pasau, David C. Blakemore, Steven V. Ley*

*Corresponding author for this work

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Abstract

Cheap and readily available aqueous formaldehyde was used as a formylating reagent in a homologation reaction with nonstabilized diazo compounds, enabled by UV photolysis of bench-stable oxadiazolines in a flow photoreactor. Various aliphatic aldehydes were synthesized along with the corresponding derivatized alcohols and benzimidazoles. No transition-metal catalyst or additive was required to affect the reaction, which proceeded at room temperature in 80 min.

Original languageEnglish
Pages (from-to)15558-15568
Number of pages11
JournalJournal of Organic Chemistry
Volume83
Issue number24
Early online date16 Nov 2018
DOIs
Publication statusPublished - 21 Dec 2018

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Chen, Y., Leonardi, M., Dingwall, P., Labes, R., Pasau, P., Blakemore, D. C., & Ley, S. V. (2018). Photochemical Homologation for the Preparation of Aliphatic Aldehydes in Flow. Journal of Organic Chemistry, 83(24), 15558-15568. https://doi.org/10.1021/acs.joc.8b02721