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

Vilhelm J. Olsson, Sara Sebelius, Nicklas Selander and Kálmán J. Szabó*

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

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

DOI: 10.1021/ja060468n

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Abstract

Allyl alcohols were regio- and stereoselectively converted to allyl boronic acids and subsequently to trifluoro(allyl)borates with tetrahydroxy diboron with high isolated yields using palladium pincer-complex catalysis. A mechanism for the fast allylic displacement of a hydroxy group is discussed.

see article for more examples

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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.

Palladium-Catalyzed Coupling of Allylboronic Acids with Iodobenzenes. Selective Formation of the Branched Allylic Product in the Absence of Directing Groups

S. Sebelius, V. J. Olsson, O. A. Wallner, K J. Szabó, J. Am. Chem. Soc., 2006, 128, 8150-8151.

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.

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Key Words

Potassium Allyltrifluoroborates

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ID: J48-Y2006-1860