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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

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

Nickel, foil, light tested, 25x25mm, thickness 0.009mm, 99.95%

Nickel, foil, 50mm disks, thickness 0.0025mm, 99.95%

Nickel, foil, 4mm disks, thickness 0.25mm, as rolled, 100%

Nickel, foil, 50mm disks, thickness 0.0075mm, 99.9%

Nickel, foil, 50mm disks, thickness 0.075mm, annealed, 99%

Nickel, foil, 5m coil, thickness 0.15mm, coil width 12mm, annealed, 99%

Nickel, foil, 50mm disks, thickness 0.25mm, annealed, 99%

Nickel, foil, 50mm disks, thickness 0.01mm, 99.95%

Nickel, foil, 5m coil, thickness 0.025mm, annealed, 99%

Nickel, foil, 5m coil, thickness 0.075mm, annealed, 99%

Nickel, foil, 50mm disks, thickness 0.25mm, as rolled, 99.99+%

Nickel, foil, 50mm disks, thickness 0.025mm, annealed, 99%

Nickel, foil, 4mm disks, thickness 0.3mm, as rolled, 100%

Nickel, foil, 5m coil, thickness 0.0125mm, 99.9%

Nickel, foil, 4mm disks, thickness 0.125mm, as rolled, 100%

Nickel, foil, 50mm disks, thickness 0.005mm, as rolled, 99.9%

Nickel, foil, 50mm disks, thickness 0.075mm, as rolled, 99.98%

Nickel, foil, 4mm disks, thickness 0.50mm, annealed, 99%

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

Nickel, rod, 500mm, diameter 20.0mm, 99%

Nickel, rod, 100mm, diameter 12.7mm, 99.98%

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

Nickel, foil, 10mm disks, thickness 0.25mm, as rolled, 99.99+%

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

Nickel, foil, 10mm disks, thickness 0.20mm, annealed, 99%

Nickel, foil, 10mm disks, thickness 0.5mm, as rolled, 100%

Nickel, foil, 10mm disks, thickness 0.05mm, as rolled, 99.99+%

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

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