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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, 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, nanopowder, <100 nm avg. part. size, ≥99% 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

Sigma-Aldrich

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

Nickel, tube, 35mm, outside diameter 7.8mm, inside diameter 6.4mm, wall thickness 0.7mm, hard, 99.5%

Nickel, foil, 0.5m coil, thickness 0.15mm, coil width 12mm, annealed, 99%

Nickel, foil, not light tested, 100x100mm, thickness 0.004mm, hard, 99%

Nickel, foil, 8mm disks, thickness 0.075mm, annealed, 99%

Nickel, foil, light tested, 100x100mm, thickness 0.038mm, 99.9%

Nickel, foil, 8mm disks, thickness 0.01mm, 99.95%

Nickel, foil, 25mm disks, thickness 0.25mm, as rolled, 99.99+%

Nickel, foil, 150x150mm, thickness 0.15mm, annealed, 99%

Nickel, foil, light tested, 100x100mm, thickness 0.05mm, 99.9%

Nickel, foil, 2m coil, thickness 0.0075mm, 99.95%

Nickel, foil, 8mm disks, thickness 0.0075mm, 99.9%

Nickel, foil, 6mm disks, thickness 0.1mm, annealed, 99%

Nickel, foil, 8mm disks, thickness 0.02mm, 99.9%

Nickel, foil, 100x100mm, thickness 1.0mm, as rolled, 99.99+%

Nickel, foil, 8mm disks, thickness 0.0125mm, 99.9%

Nickel, foil, 8mm disks, thickness 0.25mm, as rolled, 100%

Nickel, foil, 8mm disks, thickness 0.15mm, annealed, 99%

Nickel, foil, 8mm disks, thickness 0.025mm, 99.9%

Nickel, foil, 25mm disks, thickness 0.30mm, as rolled, 99.98%

Nickel, foil, light tested, 25x25mm, thickness 0.038mm, 99.9%

Nickel, foil, light tested, 150x150mm, thickness 0.05mm, annealed, 99%

Nickel, foil, 6mm disks, thickness 0.15mm, annealed, 99%

Nickel, foil, 150x150mm, thickness 0.1mm, annealed, 99%

Nickel, foil, 100x100mm, thickness 1.0mm, annealed, 99.98%