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Palladium-Catalyzed Allylic C-OH Functionalization for Efficient Synthesis of Functionalized Allylsilanes

Nicklas Selander, Jennifer R. Paasch, and Kálmán J. Szabó*

*Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden, Email: kalmanorgan.su.se

N. Selander, J. R. Paasch, K. J. Szabó, J. Am. Chem. Soc., 2011, 133, 17701-17703.

DOI: 10.1021/ja1096732


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Abstract

A palladium-catalyzed allylic silylation using allylic alcohols and disilanes as precursors proceeds smoothly under mild and neutral conditions and is suitable for synthesis of regio- and stereodefined allylsilanes. The presented silylation reaction can be easily extended to include synthesis of allylboronates by change of the dimetallic reagent.

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Direct Synthesis of Functionalized Allylic Boronic Esters from Allylic Alcohols and Inexpensive Reagents and Catalysts

G. Dutheuil, N. Selander, K. J. Szabó, V. K. Aggarwal, Synthesis, 2008, 2293-2297.


Key Words

Allylsilanes


ID: J48-Y2011-0120