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Synlett 2001; 2001(6): 0824-0826
DOI: 10.1055/s-2001-14589
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Allylsilane-Vinylcopper Reagents: Palladium-Mediated Coupling with Alkenyl Halides. Synthesis and Photochemical [2 + 2] Cyclization of (±)-Ipsdienol

Asunción Barbero* , Carlos García, Francisco J. Pulido
  • *Departamento de Química Orgánica, Universidad de Valladolid, 47011 Valladolid, Spain; Fax + 34 (983) 42 30 13; E-mail: pulido@qo.uva.es
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Publikationsdatum:
31. Dezember 2001 (online)

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Reaction of phenyldimethylsilyl-copper with 1,2-propadiene followed by Pd0 catalyzed coupling of the resulting copper intermediate with alkenyl halides affords allylsilane-containing dienes in high yield. Coupling with vinyl bromide gives 2-phenyldimethylsilylmethylbuta-1,3-diene which is an isoprenyl building block for the synthesis of (±)-Ipsenol and (±)-Ipsdienol, the aggregation pheromones of the Ips bark beetle. The photochemical [2 + 2] cyclization of Ipsdienol was also studied.

allylsilane - vinylcopper - palladium - cross-coupling - photocyclization