Abstract
We have successfully developed a novel cathodic cross-coupling reaction of aryl halides with arenes. Utilization of the cathodic single electron transfer (SET) mechanism for activation of aryl halides enables the cross-coupling reaction to proceed without the need for any transition metal catalysts or single electron donors in a mild condition. The SET from a cathode to an aryl halide initiates a radical chain by giving an anion radical of the aryl halide. The following propagation cycle also consists entirely of anion radical intermediates.
Highlights
Biaryl derivatives are considered to be useful organic compounds in industry and in the medical field [1]
Cathodic cross-coupling reaction of of aryl halides with arenes
Cross-coupling reaction of aryl halides with arenes
Summary
Biaryl derivatives are considered to be useful organic compounds in industry and in the medical field [1]. We envisioned that the cathodic reduction would be applicable for the activation of aryl halides in the initial step By this operation, an aromatic C,C cross-coupling reaction that requires neither transition metal catalyst nor single electron donor would be developed. We wish to report the realization of cathodic cross-coupling reactions of aryl halides with arenes via a single transfer (SET) pathway To overcome these electron drawbacks, we envisioned that the cathodic reduction would be applicable for (1a) and benzonitrile (2a) as in a model arylstep. By and this arene, operation, an aromatic cross-coupling substrates, werequires assumed the reaction mechanism for the nor cathodic cross-coupling as shown reaction that neither transition metal catalyst singlearomatic electronC,C donor would be developed.
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