Palladacycles as Intermediates for Selective Dialkylation of Arenes and Subsequent Fragmentation

Authors

  • Prof. Marta Catellani,

    Corresponding author
    1. Dipartimento di Chimica Organica e Industriale dell'Università Via le delle Scienze, 43100 Parma (Italy) Telefax: Int. code + (521)905472
    • Dipartimento di Chimica Organica e Industriale dell'Università Via le delle Scienze, 43100 Parma (Italy) Telefax: Int. code + (521)905472
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  • Dr. Maria Chiara Fagnola

    1. Dipartimento di Chimica Organica e Industriale dell'Università Via le delle Scienze, 43100 Parma (Italy) Telefax: Int. code + (521)905472
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  • This work was supported by the Ministero dell'Università e della Ricerca Scientifica e Tecnologica (MURST, Rome) and the Consiglio Nazionale delle Ricerche (CNR, Rome). Mass spectrometric and NMR spectroscopic facilities were provided by Centro Interfacoltà dell'Università di Parma.

Abstract

original image

Palladacycles like 1 undergo spontaneous rupture of the C–C bond between the aliphatic and aromatic parts of the norbornyl-phenyl ligand after selective meta-dialkylation of the arene ring through PdIV intermediates like 2. This reaction proceeds smoothly without β-H elimination with alkyl and benzyl halides RX.

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