4.6 Article

Visible light promoted continuous flow photocyclization of 1,2-diketones

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 19, Pages 3684-3689

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob00532k

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Funding

  1. Fondazione di Sardegna under the project Innovative antioxidant molecules for the food and health industry [CUP F71I17000180002]
  2. Sardinia Regional Government (FIR 2019)

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The continuous flow Norrish-Yang photocyclization of 1,2-diketones has been developed and used for the synthesis of a large number of functionalized 2-hydroxycyclobutanones, under blue light irradiation and employing acetone as a solvent. This eco-friendly procedure represents a valid alternative to the reactions carried out in batches thus reducing the reaction times, the formation of secondary products and simplifying the purification steps. The use of differently substituted diketone compounds has allowed us to obtain a wide range of 2 and 3-functionalized cyclobutanones, thus allowing the evaluation of the scope and limitations of this procedure.

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