Abstract
The choice of electrode material is critical for achieving optimal yields and selectivity in synthetic organic electrochemistry. The material imparts significant influence on the kinetics and thermodynamics of electron transfer, and frequently defines the success or failure of a transformation. Electrode processes are complex and so the choice of a material is often empirical and the underlying mechanisms and rationale for success are unknown. In this review, we aim to highlight recent instances of electrode choice where rationale is offered, which should aid future reaction development.
Highlights
The choice of electrode material is critical for achieving optimal yields per annum industrial process[15] that is and selectivity in synthetic organic electrochemistry
We initially summarise the most important control and change the selectivity of a reaction, and provides practical and reactivity considerations for electrode materials opportunities to vary reactivity through electrode-catalysis, in organic electrochemistry
By promoting hydrogen evolution over other potential reductive processes, the choice of cathode material influences the outcome of anodic transformations.[138,172,173]. An example of this is in the synthesis of (E)-vinylsulfones from cinnamic acids, in which Wang found a significant dependence of the reaction on the counter electrode material (Figure 12 B).[174]
Summary
The primary judgement of candidate materials will be based on their performance in the reaction, i.e., yields and selectivity, but current efficiencies, obvious signs of corrosion, cost, availability and machinability are other critical factors, the relative importance of which will vary according to the specific process. In organic synthesis where the scales are comparatively smaller, larger gains in yield or complete switches in selectivity become more important This is because the cost of the electrode material and the man-hours that are required to optimise a process must be balanced against the costs of the reagents and the value of the product. David Heard studied at the University of Sheffield (MChem, 2014) joined the Bristol Chemical Synthesis CDT at the University of Bristol He conducted his PhD research into the structural elucidation and total synthesis of maleidride natural products under the supervision of Prof. Once a material is formed into an electrode, a low ohmic resistance connection should be made
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