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Synfacts 2009(2): 0152-0152  
DOI: 10.1055/s-0028-1087500
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Silicon-Bridged Biaryls

Contributor(s): Timothy M. Swager, Jan M. Schnorr
M. Shimizu*, K. Mochida, T. Hiyama
Kyoto University, Japan
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Publication History

Publication Date:
22 January 2009 (online)

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Significance

The authors present a modular approach to silicon-bridged biaryls. Their key step is the palladium-catalyzed intramolecular direct arylation of 2-(arylsilyl)aryl triflates 7, 9 and 11. The approach is applicable to symmetrical, asymmetrical as well as heteroaromatic substrates and usually proceeds in good to excellent yields. The 2-(arylsilyl)aryl triflates were obtained by sequential silylation, retro-Brook rearrangement and triflation.