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  • Title: Cobalt-catalyzed cross addition of silylacetylenes to internal alkynes.
    Author: Sakurada T, Sugiyama YK, Okamoto S.
    Journal: J Org Chem; 2013 Apr 19; 78(8):3583-91. PubMed ID: 23510302.
    Abstract:
    A CoCl2·6H2O/Zn reagent using 2-(2,6-diisopropylphenyl)iminomethylpyridine (dipimp), 1,2-bis(diphenylphosphino)ethane (dppe), or 1,2-bis(diphenylphosphino)benzene (dppPh) as a ligand effectively catalyzed the cross-addition reaction of silylacetylene to internal alkynes. The reaction of some unsymmetrical internal alkynes, such as 3-arylpropargyl alcohols, proceeded in a highly regioselective manner in the presence of dppe or dppPh but gave a nearly 1:1 mixture of regioisomers in the presence of dipimp. The results of reactions using 1-deuterated 2-silylacetylene revealed that the reaction involves a direct oxidative addition of the silylacetylenic C-H bond to cobalt.
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