Angewandte Chemie International Edition · 2021 · 93 citations · 126 references
Herein, we disclose a straightforward, robust, and simple route to access β-substituted desaturated cyclic amines via an electrochemically driven desaturative β-functionalization of cyclic amines. This transformation is based on multiple single-electron oxidation processes using catalytic amounts of ferrocene. The reaction proceeds in the absence of stoichiometric amounts of electrolyte under mild conditions, affording the desired products with high chemo- and regioselectivity. The reaction was tolerant of a broad range of substrates and also enables late-stage β-C(sp<sup>3</sup> )-H acylation of potentially valuable products. Preliminary mechanistic studies using cyclic voltammetry reveal the key role of ferrocene as a redox mediator in the reaction.
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C-H Bond Functionalization in Complex Organic Synthesis
Kamil Godula, Dalibor Sameš · Science · 2006 · 2.1K citations
Chemical Engineering, Novel Organocatalysts, Engineering +11
Scalable and sustainable electrochemical allylic C–H oxidation
Evan J. Horn, Brandon R. Rosen, Yong Chen et al. · Nature · 2016 · 719 citations · Full text