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Synthesis 2003(17): 2671-2678
DOI: 10.1055/s-2003-42441
DOI: 10.1055/s-2003-42441
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Selectively Substituted ortho-Vinylbiphenyls by Palladium-Catalysed Reaction of ortho-Substituted Aryl Iodides with Olefins
Weitere Informationen
Received
27 June 2003
Publikationsdatum:
21. Oktober 2003 (online)
Publikationsverlauf
Publikationsdatum:
21. Oktober 2003 (online)
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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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