Synthesis of Selectively Substituted ortho-Vinylbiphenyls by Palladium-Catalysed Reaction of ortho-Substituted Aryl Iodides with Olefins

Elena Motti; Gianpietro Ippomei; Sara Deledda; Marta Catellani

doi:10.1055/s-2003-42441

PAPER

Synthesis of Selectively Substituted ortho-Vinylbiphenyls by Palladium-Catalysed Reaction of ortho-Substituted Aryl Iodides with Olefins

Elena Motti, Gianpietro Ippomei, Sara Deledda, Marta Catellani*
Dipartimento di Chimica Organica e Industriale dell’Università, Parco Area delle Scienze, 17/A, 43100 Parma, Italy
Fax: +39(0521)905472; e-Mail: marta.catellani@unipr.it;

Abstract

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Abstract

In the presence of Pd(OAc)₂ and norbornene as catalysts, ortho-substituted aryl iodides and terminal olefins react to afford selectively substituted ortho-vinylbiphenyl derivatives in good yields. The reaction proceeds through a series of steps including norbornene insertion and C-H activation with formation of palladacycles able to promote arylation of their aromatic part. Norbornene deinsertion then leads to the selective formation of a palladium-bonded biphenylyl group able to react with terminal olefins.

The one-pot process occurs under mild conditions and can be applied to a variety of aromatics and olefins.

Key words

palladium - catalysis - arylations - cross coupling - biaryls

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References

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