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

Guillaume Dutheuil, Nicklas Selander, Kálmán J. Szabó*, Varinder K. Aggarwal

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

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

DOI: 10.1055/s-2008-1067144

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Abstract

A remarkably simple and effective system allows a direct conversion of allylic alcohols into high value allylic boronic esters using commercially available reagents and catalysts.

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Direct Boronation of Allyl Alcohols with Diboronic Acid Using Palladium Pincer-Complex Catalysis. A Remarkably Facile Allylic Displacement of the Hydroxy Group under Mild Reaction Conditions

V. J. Olsson, S. Sebelius, N. Selander, K. J. Szabó, J. Am. Chem. Soc., 2006, 128, 4588-4589.

Palladium Pincer Complex Catalyzed Substitution of Vinyl Cyclopropanes, Vinyl Aziridines, and Allyl Acetates with Tetrahydroxydiboron. An Efficient Route to Functionalized Allylboronic Acids and Potassium Trifluoro(allyl)borates

S. Sebelius, V. J. Olsson, K. J. Szabó, J. Am. Chem. Soc., 2005, 127, 10478-10479.

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

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

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Key Words

allylation, allylboronates, palladium, palladacycles, transition metal

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ID: J66-Y2008-2050