Development of an electrochemical benzylic C(sp3)-H amidation reaction and 3D-printed toolkit for electrasyn expansion Anthony Choi 1 , Oliver Goodrich 2 , Matthew Edwards 2 , Alexander P. Atkins 1 , Michael W. George 2 , David M. Heard 1 , Alastair J. J. Lennox* 1 1 University of Bristol, UK, 2 University of Nottingham, UK This poster will present work from two different projects! Amides are ubiquitous and important motifs found in many drugs and natural products. [1] Although, traditional methods are robust and reliable, the necessity to develop new methods towards the synthesis of amide bonds remains important to provide flexibility when designing novel synthetic routes. Electrochemistry has provided a sustainable and selective method towards the synthesis of amides via anodic oxidation, which has been successfully applied to Ritter-type amidation reactions. [2] However, there are major limitations of this reaction which are associated with the nitrile coupling partner – mainly the availability and quantity required. To overcome these problems the use of primary amides as an alternative nucleophilic coupling partner has several advantages, such as being more widely available. The work highlighted demonstrates the use of primary amides in a novel electrochemical process to synthesise a variety of amides, which can also be scaled-up successfully in flow.
Another area of research we have also developed within recent years is the use of 3D-printing technology to build electrochemical reaction platforms for use in electrosynthetic reaction discovery. [3] Often, bespoke reactors are developed in-house for a specific purpose or are commercially available, which can offer high reproducibility and replicability by using standardized components. To bridge this divide between customizability and replicability, we have developed the Open-ESyn, a suite of 3D-printed components compatible with the popular IKA ElectraSyn. The work presented will show the development and utility of these 3D-printed components in various electrochemical reactions.
References 1. J Biotechnol , 2016 , 235 , 32–46; J Med Chem , 2020 , 63 , 12290–12358. J Am Chem Soc , 1948 , 70 , 4045–4048; 2. J Am Chem Soc , 2021 , 143 , 8597–8602; 3. Synthesis , 2023 , doi.org/10.1055/a-1992-7066; 4. Nat Commun , 2022 , 13 , 4138. ChemElectroChem , 2021 , 8 , 11, 2070-2074.
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