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Activation of Elemental Sulfur by Electrogenerated Cyanomethyl Anion: Synthesis of Substituted 2‐Aminothiophenes by the Gewald Reaction
Author(s) -
Feroci Marta,
Chiarotto Isabella,
Rossi Leucio,
Inesi Achille
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800503
Subject(s) - chemistry , acetonitrile , sulfur , catalysis , hexafluorophosphate , tetraethylammonium , electrolyte , ion , inorganic chemistry , organic chemistry , combinatorial chemistry , ionic liquid , electrode , potassium
The activation of elemental sulfur (S 8 ) has been achieved by means of electrogenerated cyanomethyl anion [easily obtained by galvanostatic reduction from acetonitrile/tetraethylammonium hexafluorophosphate (MeCN‐Et 4 NPF 6 )]. The “activated” sulfur reacted with ylidenemalononitriles to give substituted 2‐aminothiophenes in very high yields. This variation of the Gewald reaction has been carried out using only catalytic amounts of electricity and supporting electrolyte. A proposed mechanism for the interaction between S 8 and cyanomethyl anion is described.