On the chemospecificity of the double stannylation and double hydrostannation of terminal alkynes by the tributylstannane in the presence of thiol

Article abstract of DOI:10.1016/S0022-328X(97)00283-0

The mechanism of competing double stannylation and double hydrostannation reactions of terminal alkynes in the presence of arylthiol has been investigated. The data reveal the radical character of the reactions, the importance of the [tributylstannane/arylthiol] system as radical initiator at ambient temperature and the occurrence of a polarity reversal catalysis process in the double hydrostannation pathway.