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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
One-Pot Sequential Alcohol Activation and Nickel-Catalyzed Cross-Electrophile Coupling with Chlorosilanes
Xiaojie Liu1, Biping Xu1, Martin Oestreich1
1Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 115, 10623 Berlin, Germany.
Abstract:
A formal deoxygenative silylation of primary alcohols is reported. The one-pot procedure consists of an in situ bromination of the alcohol and a subsequent nickel-catalyzed cross-electrophile coupling of the formed alkyl bromide and various vinyl-substituted chlorosilanes. The key to success is the compatibility of the nickel catalysis as well as the chlorosilane electrophile with the byproducts of the preceding bromination step, especially with triphenylphosphine oxide likely acting as a weak ligand for the excess nickel catalyst used.
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