Photochemical Homologation for the Preparation of Aliphatic Aldehydes in Flow | Zendy

Yiding Chen | Zendy; Marco Leonardi | Zendy; Paul Dingwall | Zendy; Ricardo Labes | Zendy; Patrick Pasau | Zendy; David C. Blakemore | Zendy; Steven V. Ley | Zendy

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Photochemical Homologation for the Preparation of Aliphatic Aldehydes in Flow

Author(s) -

Yiding Chen,

Marco Leonardi,

Paul Dingwall,

Ricardo Labes,

Patrick Pasau,

David C. Blakemore,

Steven V. Ley

Publication year - 2018

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.8b02721

Subject(s) - chemistry , diazo , reagent , formaldehyde , photodissociation , catalysis , photochemistry , aldehyde , organic chemistry , aqueous solution , flow chemistry

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.

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