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Stereospecific Ni-catalyzed cross-coupling of potassium alkenyltrifluoroborates with alkyl halides.

Stereospecific Ni-catalyzed cross-coupling of potassium alkenyltrifluoroborates with alkyl halides.

Organic letters (2014-03-29)

Gary A Molander, O Andreea Argintaru

ABSTRACT

A general method for the alkenylation of alkyl electrophiles using nearly stoichiometric amounts of the air- and moisture-stable potassium organotrifluoroborates has been developed. Various functional groups were tolerated on both the nucleophilic and electrophilic partner. Reactions of highly substituted E- and Z-alkenyltrifluoroborates, as well as vinyl- and propenyltrifluoroborates, were successful, and no loss of stereochemistry or regiochemistry was observed.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Nickel, foil, thickness 0.5 mm, 99.98% trace metals basis

Sigma-Aldrich

Nickel, nanopowder, <100 nm avg. part. size, ≥99% trace metals basis

Sigma-Aldrich

Nickel, wire, diam. 0.5 mm, ≥99.9% trace metals basis

Sigma-Aldrich

Nickel, foil, thickness 0.1 mm, 99.98% trace metals basis

Sigma-Aldrich

Nickel, powder, <50 μm, 99.7% trace metals basis

Sigma-Aldrich

Nickel, rod, diam. 6.35 mm, ≥99.99% trace metals basis

Nickel, foil, 6mm disks, thickness 0.0125mm, 99.9%

Nickel, foil, 6mm disks, thickness 0.038mm, 99.9%

Nickel, foil, 25mm disks, thickness 0.05mm, as rolled, 99.99+%

Nickel, wire reel, 500m, diameter 0.15mm, as drawn, 99%

Nickel, foil, 6mm disks, thickness 0.007mm, 99.95%

Nickel, foil, 6mm disks, thickness 0.0125mm, annealed, 99%

Nickel, foil, 6mm disks, thickness 0.015mm, 99.9%

Nickel, foil, 6mm disks, thickness 0.025mm, as rolled, 99.99+%

Nickel, foil, 6mm disks, thickness 0.05mm, annealed, 99%

Nickel, foil, 6mm disks, thickness 0.009mm, 99.95%

Nickel, rod, 200mm, diameter 40mm, 99%

Nickel, rod, 100mm, diameter 20.0mm, 99%

Nickel, rod, 200mm, diameter 1.5mm, 99.99+%

Nickel, rod, 200mm, diameter 6.35mm, 99%

Nickel, rod, 500mm, diameter 2.0mm, 99.99+%

Nickel, rod, 200mm, diameter 10.0mm, 99.99+%

Nickel, foil, 10mm disks, thickness 0.30mm, as rolled, 99.98%

Nickel, rod, 200mm, diameter 20.0mm, 99%

Nickel, foil, 10mm disks, thickness 0.125mm, as rolled, 100%

Nickel, rod, 200mm, diameter 30mm, 99%

Nickel, foil, 15mm disks, thickness 0.0125mm, annealed, 99%

Nickel, rod, 100mm, diameter 6.35mm, 99%

Nickel, rod, 100mm, diameter 3.3mm, 99.99+%

Nickel, rod, 500mm, diameter 12.0mm, 99%