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

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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