Scalable Electrochemical Decarboxylative Olefination Driven by Alternating Polarity**

Abstract

A mild, scalable (kg) metal‐free electrochemical decarboxylation of alkyl carboxylic acids to olefins is disclosed. Numerous applications are presented wherein this transformation can simplify alkene synthesis and provide alternative synthetic access to valuable olefins from simple carboxylic acid feedstocks. This robust method relies on alternating polarity to maintain the quality of the electrode surface and local pH, providing a deeper understanding of the Hofer‐Moest process with unprecedented chemoselectivity.

A Scalable Solution to Constant-Potential Flow Electrochemistry

“…This reactor platform provides several benefits over parallel plate reactors: (1) the ability to utilize overhead stirring and appropriate impeller geometry would provide a high force of mixing in close proximity to the electrodes and greatly improve the mass transport; (2) impeller-based mixing is compatible with biphasic reaction mixtures; (3) the use of rod-based electrodes allows for interchanging of electrode materials with relative ease; and (4) a balanced A / V ratio allows for complete control over current density and residence time, the two most important scale-up parameters. Previously, we disclosed this reactor design, which was amenable to use in rapidly alternating polarity (rAP) electrochemical reactions in batch up to 1 kg scale. ,, Indeed, in the 3 years that we have evaluated this design for electrochemical reactions, we have seen these benefits in direct comparison to several alternative reactor designs.…”

Simplifying Access to Targeted Protein Degraders via Nickel Electrocatalytic Cross‐Coupling

“…occasions. [29,[38][39][40] As such, GCC could be scaled up on gramscale in batch or flow modes without any yield diminishment (Figure 2). The only modification made to the general procedure was scaling the current linearly to the amount of substrate employed (30 mA/mmol).…”

Overview of Recent Scale-Ups in Organic Electrosynthesis (2000–2023)

“…132 A key milestone in demonstrating kilogram-scale alternating polarity (AP) electrolysis in batch was achieved by AbbVie and the Baran group in 2023. 133 The team successfully scaled up a decarboxylative olefination of 59 (Scheme 22) using an 8 L jacketed glass vessel equipped with 96 graphite rods (48 as anodes and 48 as cathodes). The transformation provided a 5:1 ratio of products 60 and 61 in 80% yield.…”