Merck

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

Organic letters (2014-03-29)
Gary A Molander, O Andreea Argintaru
RESUMEN

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.

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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, 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, foil, thickness 0.5 mm, 99.98% trace metals basis
Sigma-Aldrich
Nickel, rod, diam. 6.35 mm, ≥99.99% trace metals basis
Nickel, mesh, 240x240mm, nominal aperture 0.43mm, thickness 0.004mm, wire diameter 0.067mm, 51 wires/inch, open area 75%, electro-formed mesh, 99.9%
Nickel, foil, 2m coil, thickness 0.5mm, annealed, 99.98%
Nickel, foil, 50x50mm, thickness 2.0mm, annealed, 99%
Nickel, insulated wire, 20m, conductor diameter 0.025mm, insulation thickness 0.0035mm, polyimide insulation
Nickel, foil, 2m coil, thickness 0.025mm, coil width 600mm, as rolled, 99%
Nickel, mesh, 30x30mm, nominal aperture 0.04mm, thickness 0.004mm, wire diameter 0.011mm, 500 wires/inch, open area 60%, electro-formed mesh, 99.9%
Nickel, foil, not light tested, 45x45mm, thickness 0.004mm, hard, 99.98%
Nickel, foil, light tested, 25x25mm, thickness 0.025mm, annealed, 99%
Nickel, foil, light tested, 50x50mm, thickness 0.05mm, as rolled, 99.99+%
Nickel, foil, 2m coil, thickness 0.02mm, 99.9%
Nickel, foil, not light tested, 25x25mm, thickness 0.004mm, 99.95%
Nickel, foil, light tested, 50x50mm, thickness 0.03mm, 99.9%
Nickel, mesh, 260x260mm, nominal aperture 0.34mm, thickness 0.025mm, wire diameter 0.041mm, 70 wires/inch, open area 80%, electro-formed mesh, 99.9%
Nickel, foil, 2m coil, thickness 0.05mm, 99.9%
Nickel, foil, light tested, 50x50mm, thickness 0.05mm, annealed, 99%
Nickel, foil, 25x25mm, thickness 0.125mm, as rolled, 99.99+%
Nickel, foil, not light tested, 150x150mm, thickness 0.008mm, 99.95%
Nickel, foil, light tested, 50x50mm, thickness 0.01mm, 99.95%
Nickel, foil, 10mm disks, thickness 0.05mm, 99.9%
Nickel, tube, 500mm, outside diameter 2.5mm, inside diameter 2.25mm, wall thickness 0.125mm, hard, 99.5%
Nickel, foil, not light tested, 25x25mm, thickness 0.004mm, hard, 99%
Nickel, rod, 1000mm, diameter 6.35mm, 99%
Nickel, foil, not light tested, 25x25mm, thickness 0.003mm, 99.95%
Nickel, mesh, 30x30mm, nominal aperture 0.43mm, thickness 0.004mm, wire diameter 0.067mm, 51 wires/inch, open area 75%, electro-formed mesh, 99.9%