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Keywords:

  • density functional calculations;
  • hydrostannation;
  • radical ions;
  • reaction mechanisms;
  • regioselectivity
Thumbnail image of graphical abstract

Not as radical as you think: The free-radical hydrostannylation of alkynes has been extensively studied and while every published mechanism involves solely radical intermediates, this appears not to be correct. Trace molecular oxygen is necessary for any radical-mediated hydrostannylation to occur with a wide selection of alkynes, thus leading to a proposed hybrid single-electron transfer/radical propagation mechanism. AIBN=2,2′-azobis(2-methylpropionitrile).