Synlett 2005(16): 2513-2515  
DOI: 10.1055/s-2005-872699
LETTER
© Georg Thieme Verlag Stuttgart · New York

Selective Functionalization of Arenes through the Reaction of Aryne-Zirconocene Complexes and Enol Ethers

José Barluenga*, Amadeo Fernández, Lucía Álvarez-Rodrigo, Félix Rodríguez, Francisco J. Fañanás
Instituto Universitario de Química Organometálica ‘Enrique Moles’, Unidad Asociada al C.S.I.C., Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo, Spain
Fax: +34(98)5103450; e-Mail: barluenga@uniovi.es;
Further Information

Publication History

Received 2 June 2005
Publication Date:
21 September 2005 (online)

Abstract

A new method for the selective functionalization of aromatic rings by the zirconium promoted cross coupling reaction of an aryllithium compound and an enol ether is reported. Formation of an aryne-zirconocene complex and its regioselective coupling with an enol ether are the key steps of the process. This methodology allows the synthesis of functionalized styrene or Z-alkenol derivatives from simple and easily available starting materials.