Electrochemistry is a powerful tool for the activation and derivatization of molecules in the search for novel pharmaceutically relevant structures. We have considerable experience in the rapid screening of scope and conditions using the IKA ElectraSyn 2.0 package. These reactions can be utilized efficiently for the synthesis of relatively complex intermediates and final products.
Multi-vial screening setup for electrochemical reactions using the Elektrasyn 2.0
Inspired by literature such as that published by Tim Noël[1], Phil Baran[2] and many others, electrosynthetic methodologies applied in our research now include the direct C-sp3 fluorination[3] of semicomplex molecules, desaturation of ketones, and mild aromatization conditions.
Reactions in our toolbox include C–H activation via the Shono oxidation of tertiary and secondary N-carbamates, amides, and lactams, or non-Kolbe decarboxylation as an efficient way to incorporate three dimensionality and complexity to simple substrates. The reaction has been applied to both early and late-stage derivatization of natural-product-like and known lead-like analogs. After optimization on a small scale, these conditions were utilized in the synthesis of many substrates on multimole scale using our electrochemical reactors.
An example of the synthesis of a building block is depicted in the scheme below. This reaction was performed on 0.5 kg scale in our custom-built multipurpose reactor using the following conditions:
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[1] Noël, T. et. al., The Fundamentals Behind the Use of Flow Reactors in Electrochemistry, Acc. Chem. Res. 2019, (10), 2858–2869, Link
[2] Gnaim, S. et. al., Electrochemically driven desaturation of carbonyl compounds, Nat. Chem. 2021, 4, 367-372, Link
[3] Takahira, Y. et. al., Electrochemical C(sp3)-H Fluorination, Synlett 2019, 10, 1178-1182, Link
