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Pure Appl. Chem., 2002, Vol. 74, No. 1, pp. 63-68

Selective organometallic syntheses from molecular pools

Marta Catellani

Dipartimento di Chimica Organica e Industriale dell'Università, Parco Area delle Scienze, 17/A, 43100 Parma, Italy

Abstract: A new methodology is described, consisting of the use of molecular pools in palladium-catalyzed sequential processes occurring under mild conditions with high selectivity. These reactions involve palladacycle formation from aryl iodide, palladium, and norbornene, the latter behaving as a second catalyst that is first incorporated into the metallacycle and expelled at the end of the process. Selective alkylation or arylation of the arene nucleus occurring by oxidative addition/reductive elimination of palladacycles are coupled, after norbornene expulsion, with C­H or C­C bond-forming reactions such as hydrogenolysis, olefin insertion, arylboronic coupling, etc. The variety of possible combinations offers a powerful tool for the selective synthesis of unusual and not readily accessible aromatics.