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Synthesis 1994; 1994(6): 583-591
DOI: 10.1055/s-1994-25528
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Palladium(0)-Catalyzed Coupling Reactions of 2-Alkoxy-1-ethynylcyclopropanes with Aryl and Ethenyl Halides: Preparation of Cyclopropyl Substituted Ethynylarenes, Eneynes and Enediynes

Gregory Mcgaffin* , Armin de Meijere
  • *Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstraße 2, D-37077 Göttingen, Germany
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Publication Date:
17 September 2002 (online)

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2-Alkoxy-1-ethynylcyclopropanes 1-R 1, readily available in diastereo- and enantiopure form, 2,3 undergo facile palladium-catalyzed cross-coupling reactions with various mono- and oligohaloarenes 2(a-c)-X, 4, 6, 9, 12, haloalkenes 14a-d and (E/Z)-1,2-dihaloethenes [(E/Z)-18-X]. The trans- and trans/cis-(2-alkoxycyclopropyl)-ethynyl derivatives 3(a-c)-R 1, 5, 7, 10, 13, 15a-d and (E)-19(22) were exclusively obtained in good to excellent yields. The coupling reaction thus opens the first direct access to configurationally uniform (2-alkoxycyclopropyl)ethynyl substituted arenes, and 2-alkoxycyclopropyl substituted eneynes and enediynes. Catalytic hydrogenation of ethynylarenes 3(a-c)-R 1, 10, and 13 smoothly afforded the corresponding (E/Z)-[(2-alkoxycyclopropyl) ethenyl]arenes 24(a-c)-R 1, 25 and 26, which are not directly accessible by palladium(0)-catalyzed coupling reactions of (E)-2-alkoxy-1-ethenylcyclopropanes with haloarenes.