Journal
GREEN CHEMISTRY
Volume 18, Issue 13, Pages 3767-3774Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6gc00666c
Keywords
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Funding
- National Natural Science Foundation of China [21272021, 21472011]
- National Key Technology RD Program [2011BAD23B01]
- US National Science Foundation [OISE-0968399]
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An efficient paired electrosynthesis involving C-H functionalization and subsequent C-S and C-N bond formation for the assembly of valuable3-amino-2-thiocyanato-alpha,beta-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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