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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

Nickel, wire reel, 20m, diameter 0.05mm, as drawn, 99%

Nickel, wire reel, 50m, diameter 0.25mm, annealed, 99%

Nickel, foil, not light tested, 45x45mm, thickness 0.004mm, hard, 99.98%

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

Nickel, foil, 50mm disks, thickness 0.125mm, as rolled, 99.99+%

Nickel, foil, 1m coil, thickness 0.075mm, annealed, 99%

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

Nickel, wire reel, 50m, diameter 0.5mm, as drawn, 99%

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

Nickel, foil, 1m coil, thickness 0.5mm, annealed, 99.98%

Nickel, foil, 5m coil, thickness 0.05mm, annealed, 99%

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

Nickel, rod, 500mm, diameter 12.0mm, 99%

Nickel, rod, 100mm, diameter 12.0mm, 99%

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

Nickel, tube, 1000mm, outside diameter 0.8mm, inside diameter 0.3mm, wall thickness 0.25mm, as drawn, 99.5%

Nickel, rod, 200mm, diameter 20.0mm, 99%

Nickel, foil, 10mm disks, thickness 0.30mm, as rolled, 99.98%

Nickel, foil, 1m coil, thickness 1.0mm, annealed, 99.98%

Nickel, foil, 20m coil, thickness 0.125mm, coil width 1mm, as rolled, 99%

Nickel, tube, 100mm, outside diameter 2.5mm, inside diameter 2mm, wall thickness 0.25mm, hard, 99.5%

Nickel, rod, 100mm, diameter 16mm, 99.99+%

Nickel, foil, 10mm disks, thickness 0.05mm, as rolled, 100%

Nickel, tube, 1000mm, outside diameter 1.0mm, inside diameter 0.2mm, wall thickness 0.4mm, hard, 99.5%

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

Nickel, tube, 100mm, outside diameter 0.35mm, inside diameter 0.3mm, wall thickness 0.025mm, hard, 99.5%

Nickel, sphere, 100pcs, diameter 3.0mm, precision sphere grade 200, 99%

Nickel, tube, 200mm, outside diameter 3.25mm, inside diameter 3.05mm, wall thickness 0.1mm, hard, 99.5%

Nickel, tube, 100mm, outside diameter 2.8mm, inside diameter 1.8mm, wall thickness 0.5mm, hard, 99.5%