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

Sara Sebelius, Vilhelm J. Olsson, Olov A. Wallner and Kálmán J. Szabó*

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

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

DOI: 10.1021/ja062585o

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Abstract

Palladium-catalyzed coupling reactions of functionalized allylboronic acids with various iodobenzenes under standard Suzuki-Miyaura coupling conditions afforded selectively the branched allylic products in high to excellent yields.

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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.

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Key Words

Allylboronic Acids, Allylic Substitution

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ID: J48-Y2006-2150