Overcoming Limitations in Decarboxylative Arylation via Ag-Ni Electrocatalysis

A useful protocol for achieving decarboxylative cross-coupling (DCC) of redox-active esters (RAE, isolated or generated in situ) and halo(hetero)arenes is reported. This pragmatically focused study employs a unique Ag-Ni electrocatalytic platform to overcome numerous limitations that have plagued this strategically powerful transformation. In its optimized form, coupling partners can be combined in a surprisingly simple way: open to the air, using technical-grade solvents, an inexpensive ligand and Ni source, and substoichiometric AgNO3, proceeding at room temperature with a simple commercial potentiostat. Most importantly, all of the results are placed into context by benchmarking with state-of-the-art methods. Applications are presented that simplify synthesis and rapidly enable access to challenging chemical space. Finally, adaptation to multiple scale regimes, ranging from parallel milligram-based synthesis to decagram recirculating flow is presented.

Automated summary

A practical protocol for decarboxylative cross-coupling of redox-active esters and halo(hetero)arenes is reported. This study overcomes several limitations in this transformation and provides benchmarking with state-of-the-art methods, demonstrating its importance and potential applications in accessing challenging chemical space. The protocol is adaptable to different scales of synthesis.