Download PDF
Synthesis 2001; 2001(2): 0251-0261
DOI: 10.1055/s-2001-10808
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Conversion of Iodocyclopropanes into Cyclopropylzinc Chlorides and Pd(0)-Catalyzed Cross-Coupling of the Latter Derivatives with Alkenyl Iodides and Iodobenzene: Stereospecific Synthesis of 1,2-Bisalkenylcyclopropanes and 1-Alkenyl-2-phenylcyclopropanes

Edward Piers* , Philip D. G. Coish
  • *Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, V6T 1Z1 Canada; Fax +1(604)8222847; E-mail: epier§interchange.ubc.ca
Further Information

Publication History

Publication Date:
31 December 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

A method for the preparation of functionalized cyclopropylzinc chlorides, which involves treatment of substituted 2-alkenyl-1-iodocyclopropanes with BuLi followed by transmetalation of the resultant cyclopropyllithium with zinc chloride, is described. Palladium(0)-catalyzed cross-coupling of the cyclopropylzinc chloride derivatives with alkenyl iodides or iodobenzene provides highly substituted 1,2-bisalkenylcyclopropanes or 1-alkenyl-2-phenylcyclopropanes. In two of the cases studied, the initially formed cis-1,2-bisalkenylcyclopropanes 27, 29 underwent partial Cope rearrangement under the cross-coupling conditions to afford the corresponding 1,4-cycloheptadienes 28 and 30, respectively.

palladium - cross-coupling - iodocyclopropanes - 1,2-bisalkenylcyclopropanes - rearrangements