Organic Chemistry

Overcoming Limitations in Decarboxylative Arylation via Ag-Ni Electrocatalysis

Authors

Abstract

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, technical grade solvents, an inexpensive ligand and Ni source, 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 mg-based synthesis to decagram recirculating flow is presented

Content

Thumbnail image of Archive Text Final Endnote Delinked.pdf

Supplementary material

Thumbnail image of SI FINAL Endnote Delinked.pdf
Supporting Information
Procedures and Spectral Data