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Pure Appl. Chem. Vol.
74, No. 1, pp. 63-68 (2002)
Pure and Applied Chemistry
Vol. 74, Issue 1
Selective organometallic syntheses from molecular pools*
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.
*Lecture presented at the 11th IUPAC International
Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
(OMCOS-11), Taipei, Taiwan, 22-26 July 2001. Other presentations are
presented in this issue, pp.1-186.
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