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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, foil, thickness 0.5 mm, 99.98% trace metals basis
Sigma-Aldrich
Nickel, rod, diam. 6.35 mm, ≥99.99% trace metals basis
Sigma-Aldrich
Nickel, wire, diam. 0.5 mm, ≥99.9% trace metals basis
Nickel, foil, 4mm disks, thickness 0.5mm, annealed, 99.98%
Nickel, foil, 4mm disks, thickness 0.20mm, annealed, 99%
Nickel, foil, 5m coil, thickness 0.075mm, annealed, 99%
Nickel, foil, 50mm disks, thickness 0.25mm, annealed, 99%
Nickel, foil, 50mm disks, thickness 0.01mm, 99.95%
Nickel, foil, 50mm disks, thickness 0.125mm, as rolled, 99.99+%
Nickel, foil, 4mm disks, thickness 0.25mm, annealed, 99%
Nickel, foil, 4mm disks, thickness 0.50mm, annealed, 99%
Nickel, foil, 4mm disks, thickness 0.075mm, annealed, 99%
Nickel, foil, 5m coil, thickness 0.025mm, annealed, 99%
Nickel, foil, 4mm disks, thickness 0.25mm, as rolled, 100%
Nickel, foil, 50mm disks, thickness 0.075mm, as rolled, 99.98%
Nickel, foil, 50mm disks, thickness 0.25mm, as rolled, 99.99+%
Nickel, foil, 5m coil, thickness 0.0125mm, 99.9%
Nickel, foil, 5m coil, thickness 0.15mm, coil width 12mm, annealed, 99%
Nickel, foil, 50mm disks, thickness 0.025mm, annealed, 99%
Nickel, foil, 50mm disks, thickness 0.038mm, 99.9%
Nickel, foil, 50mm disks, thickness 0.025mm, 99.9%
Nickel, foil, 4mm disks, thickness 0.125mm, as rolled, 100%
Nickel, foil, 50mm disks, thickness 0.03mm, 99.9%
Nickel, foil, 5m coil, thickness 0.05mm, annealed, 99%
Nickel, foil, 50mm disks, thickness 0.15mm, annealed, 99%
Nickel, foil, 50mm disks, thickness 0.0125mm, 99.99+%
Nickel, foil, 50mm disks, thickness 0.0025mm, 99.95%