Ultra‐Fast Continuous‐Flow Photo‐Thiol‐Ene Functionalization of Conformation‐Controlled Cinchona Alkaloids - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2022

Ultra‐Fast Continuous‐Flow Photo‐Thiol‐Ene Functionalization of Conformation‐Controlled Cinchona Alkaloids

Résumé

In this work, we describe ultra-fast continuous flow photo-thiolene reactions on cinchona alkaloids derivatives through a control of the reactive conformation in solution. Flow thiol-ene reactions proceed at 32 °C under light irradiation at 365 nm and require only 2.5 minutes of residence time to reach completion. The short path length of the tubular flow photochemical reactor, which maximizes and homogenizes the photon flux, associated to the fine tuning of the reactive conformation of cinchona alkaloids in solution are the main reasons for the high rates observed. The predominant conformation in solution of cinchona alkaloids was adjusted through the substitution of the hydroxyl group at C9 by a phenyl carbamate function.

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Chimie
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Dates et versions

hal-04016364 , version 1 (06-03-2023)

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Kouakou Eric Konan, Abollé Abollé, François‐xavier Felpin. Ultra‐Fast Continuous‐Flow Photo‐Thiol‐Ene Functionalization of Conformation‐Controlled Cinchona Alkaloids. European Journal of Organic Chemistry, 2022, 26 (1), pp.e202201055. ⟨10.1002/ejoc.202201055⟩. ⟨hal-04016364⟩
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