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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

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

Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden

J. Am. Chem. Soc., 2006, 128 (14), pp 4588–4589

DOI: 10.1021/ja060468n

Publication Date (Web): March 22, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, kalman@organ.su.se

Abstract

Allyl alcohols were converted to allyl boronic acids and subsequently to trifluoro(allyl)borates with tetrahydroxy diboron using palladium pincer-complex catalysis. These reactions are regio- and stereoselective proceeding with high isolated yields. Competitive boronation experiments indicate that under the applied reaction conditions the allylic displacement of a hydroxy group is faster than the displacement of an acetate leaving group. It is assumed that the hydroxy group of the allyl alcohol is converted to a diboronic acid ester functionality, which can easily be substituted.

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Published In Issue April 12, 2006
Received January 20, 2006

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Communication

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

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

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

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

Petasis Borono-Mannich Reaction and Allylation of Carbonyl Compounds via Transient Allyl Boronates Generated by Palladium-Catalyzed Substitution of Allyl Alcohols. An Efficient One-Pot Route to Stereodefined α-Amino Acids and Homoallyl Alcohols

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