Reaction of Aromatic Carbonyl Compounds with Silylborane Catalyzed by Au Nanoparticles: Silylative Pinacol-type Reductive Dimerization via a Radical Pathway

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Abstract
Aromatic aldehydes and acetophenones undergo silylative pinacol-type reductive dimerization in their reaction with silylborane pinB-SiMe2Ph (pin: pinacolato) catalyzed by supported Au nanoparticles on TiO2. It is proposed that after initial activation of silylborane by Au nanoparticles and addition to the carbonyl functionality of an aromatic aldehyde or ketone, an aryl silyloxy radical is generated from the collapse of the intermediate adduct, which then dimerizes through a chain process. The silyloxy radical was almost quantitatively trapped, in the presence of TEMPO.
Funding Information
  • General Secretariat for Research and Innovation (31449)
  • Hellenic Foundation for Research and Innovation

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