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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, nanopowder, <100 nm avg. part. size, ≥99% trace metals basis
Sigma-Aldrich
Nickel, powder, <50 μm, 99.7% trace metals basis
Sigma-Aldrich
Nickel, foil, thickness 0.1 mm, 99.98% trace metals basis
Sigma-Aldrich
Nickel, wire, diam. 0.5 mm, ≥99.9% 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, foil, 15mm disks, thickness 0.075mm, annealed, 99%
Nickel, tube, 100mm, outside diameter 0.75mm, inside diameter 0.59mm, wall thickness 0.08mm, hard, 99.5%
Nickel, foil, 10mm disks, thickness 0.30mm, as rolled, 99.98%
Nickel, foil, 1m coil, thickness 0.15mm, annealed, 99%
Nickel, rod, 200mm, diameter 20.0mm, 99%
Nickel, foil, 10mm disks, thickness 0.125mm, as rolled, 100%
Nickel, foil, 1m coil, thickness 0.3mm, coil width 1mm, as rolled, 99%
Nickel, sphere, 100pcs, diameter 0.76mm, precision sphere grade 200, 99%
Nickel, rod, 500mm, diameter 9.5mm, 99%
Nickel, foil, 15mm disks, thickness 0.25mm, as rolled, 100%
Nickel, tube, 100mm, outside diameter 3.25mm, inside diameter 3.05mm, wall thickness 0.1mm, hard, 99.5%
Nickel, tube, 100mm, outside diameter 0.8mm, inside diameter 0.5mm, wall thickness 0.15mm, as drawn, 99.5%
Nickel, tube, 1000mm, outside diameter 3.0mm, inside diameter 2.4mm, wall thickness 0.3mm, hard, 99.5%
Nickel, foil, 1m coil, thickness 0.003mm, 99.95%
Nickel, foil, 15mm disks, thickness 0.5mm, as rolled, 99.99+%
Nickel, rod, 50mm, diameter 5.0mm, 99.99+%
Nickel, tube, 100mm, outside diameter 2.5mm, inside diameter 2mm, wall thickness 0.25mm, hard, 99.5%
Nickel, tube, 200mm, outside diameter 0.65mm, inside diameter 0.384mm, wall thickness 0.133mm, as drawn, 99.5%
Nickel, tube, 100mm, outside diameter 0.35mm, inside diameter 0.3mm, wall thickness 0.025mm, hard, 99.5%
Nickel, foil, 1m coil, thickness 0.125mm, annealed, 99.98%
Nickel, foil, 10mm disks, thickness 0.3mm, as rolled, 100%
Nickel, foil, 15mm disks, thickness 0.025mm, annealed, 99%
Nickel, rod, 50mm, diameter 10.0mm, 99.99+%
Nickel, tube, 200mm, outside diameter 7.11mm, inside diameter 6.57mm, wall thickness 0.27mm, hard, 99.5%