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Pure Appl. Chem., 2005, Vol. 77, No. 7, pp. 1243-1248

New catalytic methods for the synthesis of selectively substituted aromatics through palladacycles

Marta Catellani1, Elena Motti1, Fiorenza Faccini1 and Raffaella Ferraccioli2

1 Dipartimento di Chimica Organica e Industriale dell’Università and CIRCC, Parco Area delle Scienze, 17/A, 43100 Parma, Italy
2 CNR, Istituto di Scienze e Tecnologie Molecolari (ISTM), Via C. Golgi 19, 20133 Milano, Italy

Abstract: Joint palladium and norbornene catalysis for selective aromatic functionalization via palladacycles is reported. Both alkylation and arylation of aromatics are considered after a brief outlook on the mechanism. These are multistep reactions that proceed in ordered sequences and are chemio-, regio-, and stereoselective. The study of the single steps with isolation of the organometallic species involved has allowed us to detect subtle steric and electronic effects which have been exploited to achieve catalytic reactions. Recent developments of aromatic alkylation and arylation are reported, in particular, condensed heterocyclic ring formation involving dialkylated arylpalladium complexes or both symmetrically and unsymmetrically substituted biphenylylpalladium complexes.