SCHEDULED MAINTENANCE
Electrochemical C–H functionalization and subsequent C–S and C–N bond formation: paired electrosynthesis of 3-amino-2-thiocyanato-α,β-unsaturated carbonyl derivatives mediated by bromide ions†
Abstract
An efficient paired electrosynthesis involving C–H functionalization and subsequent C–S and C–N bond formation for the assembly of valuable 3-amino-2-thiocyanato-α,β-unsaturated carbonyl derivatives has been developed. In the paired electrolysis, the amino and thiocyanato moieties originate from a single reagent or a combination of ammonium acetate and potassium isocyanate. The chemistry proceeds in a simple undivided cell employing a sub-stoichiometric amount of NH4Br that serves both as an inner sphere type redox catalyst and a supporting electrolyte; in this manner an additional conducting salt is not required. The reaction also works using a catalytic amount of NH4Br. Cyclic voltammetry and the results of control experiments demonstrate that the reaction proceeds via an anodically initiated C–H functionalization of the 1,3-dicarbonyl substrates that occurs via the electrochemical oxidation of bromide and simultaneous cathodic reduction of ammonium ions.
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