Gold-Mediated Hydrohydrazination

  • Author: Andrei Dragan
  • Published Date: 03 February 2017
  • Source / Publisher: Chemistry – An Asian Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Gold-Mediated Hydrohydrazination

Gold complexes have useful applications in catalysis, organic synthesis, and biomedicine. Daniel Mendoza-Espinosa, Guillermo E. Negrón‐Silva, Universidad Autonoma Metropolitana, Azcapotzalco, Mexico, and colleagues have developed a visible light-promoted Au(I) to Au(III) oxidation in triazol-5-ylidene complexes (MIC).


The team prepared a series of MICs of the formula MIC(CH2)n·AuI with (n = 1–3) via a one-pot reaction of triazolium precursors with potassium hexamethyl disilazide (KHMDS) and AuCl(SMe2). Exposing chloroform solutions of the gold(I) complexes to visible light resulted in a spontaneous disproportionation process which resulted in cationic gold(III) complexes of the type [{MIC(CH2)n}2·AuI2]+I.


All complexes were characterized and both the Au(I) and Au(III) series were tested in the catalytic hydrohydrazination of terminal alkynes using hydrazine as a nitrogen source. It was observed that although both series successfully generated the products using 3 mol% catalyst loading at 80 °C in toluene, the combination of MIC-Au(I) complexes with KB(C6F5)4 as an additive displayed the best performance of the series.


 

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