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Synlett 1999; 1999(3): 375
DOI: 10.1055/s-1999-6185
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Zirconocene Dichloride and Related Reagents

Urs H. Hirt*
  • *Institut für Organische Chemie der Universität Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland
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Publication Date:
31 December 1999 (online)

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Although chemistry with arenes has a long tradition in organic synthesis, the use of transition metal containing reagents can lead to completely new reactivities and therefore to new functionalization strategies. One of the first syntheses of an aryne zirconocene complex of type 4 was published by Erker et al.

Bis(cyclopentadienyl)zirconium dichloride 1 is a commercially available and stable compound. It reacts in transmetallation reactions, either with t-BuLi, followed by a rearrangement to 2a, or with trimethylaluminium, to 2b. Treatment of 2 with a lithiated arene results in zirconocene aryne complexes of type 4. They react with different alkenes and alkynes yielding 1,2-bis-functionalized arenes. The complexation and insertion properties of chiral zirconium compounds of type 3 with alkenes can also be used in stereoselective reactions.