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Photochemistry

Paternò–Büchi pathways

Nature Synthesis volume 2, pages 9–10 (2023)Cite this article

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The Paternò–Büchi reaction is a useful approach in organic synthesis to prepare oxetanes. Understanding the mechanism of this reaction is required for the prediction and control of the diastereoselectivity of the products.

Photochemical reactions are an important tool in organic synthesis and in the chemical and pharmaceutical industry, where these reactions are particularly useful in the search for biologically active compounds. The reason for this success in different applications is that, upon electronic excitation by light absorption, or by energy transfer in the case of photochemical sensitization, the electronic configuration of a compound changes and thus the chemical reactivity changes1. This means that compounds or compound families that are difficult to, or cannot be, synthesized by conventional methods become available under photochemical conditions. Traditionally, organic photochemistry is closely linked to physical chemistry2. This is because techniques such as time-resolved spectroscopy are often used for mechanistic studies, for example, to understand electron transfer processes or to detect and characterize intermediates in these reactions. In recent years, the technology of photochemical reactors has been developed to increase the efficiency of photochemical reactions, such as by reducing the optical trajectory to increase the concentration of the chromophore as well as through the development of continuous flow to further optimize the reactions.

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Fig. 1: Mechanisms of the Paternò–Büchi reaction.

References

  1. Klán, P. & Wirz, J. Photochemistry of Organic Compounds: From Concepts to Practice (John Wiley & Sons, 2009).

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  1. Twitter: @PhotochemistryT

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  1. CNRS, Université de Reims Champagne-Ardenne, ICMR, Equipe de Photochimie, UFR Sciences, Reims, France

    Norbert Hoffmann

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  1. Norbert Hoffmann
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Correspondence to Norbert Hoffmann.

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The author declares no competing interests.

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Hoffmann, N. Paternò–Büchi pathways. Nat. Synth 2, 9–10 (2023). https://doi.org/10.1038/s44160-022-00200-7

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