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Synthesis 1999; 1999(4): 629-634
DOI: 10.1055/s-1999-3449
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Water as a Proton Source in Regio- and Chemoselective Stannylcupration of Alkynes and Enynes

Jean-François Betzer* , Ange Pancrazi
  • *Laboratoire de Synthèse Organique, CNRS, Ecole Polytechnique, DCSO, F-91128, Palaiseau, France; Fax +33(1)69 33 30 10; E-mail: pancrazi@poly.polytechnique.fr
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Publication Date:
31 December 1999 (online)

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Stannylcupration of silylated alkynes or enynes does not proceed under classic conditions, but in the presence of methanol as a proton source the silyl group was removed and stannylation takes place. In order to preserve the silylated alkyne function, stannylcuprations of methyl-substituted alkyne 5 or enynes 12 and 16 were carried out in a competitive reaction in the presence of water in the cuprate solution. High yields and total regio-, stereo- and chemoselectivity were observed and the silylated alkyne function was preserved under these conditions.

stannylcupration - proton source - water - chemoselectivity - trimethylsilyl alkynes - vinyl tin - dienyltin

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