Abstract
A continuous‐flow synthesis of aziridines by palladium‐catalyzed C(sp3)−H activation is described. The new flow reaction could be combined with an aziridine‐ring‐opening reaction to give highly functionalized aliphatic amines through a consecutive process. A predictive mechanistic model was developed and used to design the C−H activation flow process and illustrates an approach towards first‐principles design based on novel catalytic reactions.
Highlights
A continuous-flow synthesis of aziridines by palladium-catalyzed C(sp3)ÀH activation is described
It is noticeable that the transition of novel catalytic transformations of potential industrial interest into continuous flow processes is often slow owing to the inherent complexity of the reaction systems
Part of the reason for this deficiency is the limited mechanistic understanding of these complex reactions, which frequently are heterogeneous under operating conditions; this characteristic can preclude industrial applications of either batch or continuous CÀH
Summary
A continuous-flow synthesis of aziridines by palladium-catalyzed C(sp3)ÀH activation is described. We discovered that the addition of acetic acid to the reaction mixture for the palladium-catalyzed CÀH activation to form aziridines resulted in a significant rate enhancement.[7] We chose these conditions from which to develop a predictive kinetic model that would facilitate the transfer from batch to flow processes.
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