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Synlett 2001; 2001(1): 0123-0125
DOI: 10.1055/s-2001-9709
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Unusual Cleavage of the Enolsilane C-O Bond: Transformation of 2-Silyloxy-1,3-dienes into 1,3-Dienyl-2-zirconium Compounds and their Cross-Coupling Reactions

Benjamin Ganchegui* , Philippe Bertus, Jan Szymoniak
  • *Réactions Sélectives et Applications, CNRS and Université de Reims, 51687 Reims Cedex 2, France; Fax +33-3-26 91 31 66; E-mail: jan.szymoniak@univ-reims.fr
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Publication Date:
31 December 2001 (online)

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Aryl enolsilanes and 2-silyloxy-1,3-dienes react with zirconocene to give alkenylzirconium, and novel 1-methylene-2-propenylzirconium compounds which can be used as 2-dienylation reagents. Thus, one-pot coupling of 4-phenyl-1,3-butadienyl-2-zirconocene (2d) with a range of electrophiles including aryl, alkynyl, allyl halides, bromine, iodine and a Michael acceptor occurs regioselectively at the C-2 position in the presence of Pd or Cu catalysts.

silyloxydienes - zirconium - dienylzirconocenes - cross-coupling