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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

Nickel, foil, 10mm disks, thickness 0.025mm, 99.9%

Nickel, foil, 10m coil, thickness 0.05mm, coil width 2mm, annealed, 99%

Nickel, foil, 10mm disks, thickness 0.0125mm, annealed, 99%

Nickel, foil, 50x50mm, thickness 0.3mm, as rolled, 99.999%

Nickel, foil, 50x50mm, thickness 1.0mm, annealed, 99%

Nickel, tube, 500mm, outside diameter 3.25mm, inside diameter 3.05mm, wall thickness 0.1mm, hard, 99.5%

Nickel, tube, 500mm, outside diameter 2.5mm, inside diameter 2mm, wall thickness 0.25mm, hard, 99.5%

Nickel, rod, 1000mm, diameter 2.0mm, 99.99+%

Nickel, foil, 2m coil, thickness 0.5mm, annealed, 99.98%

Nickel, foil, 50x50mm, thickness 2.0mm, annealed, 99%

Nickel, foil, 50x50mm, thickness 0.25mm, as rolled, 99.99+%

Nickel, pellets, 20g, max. size 5mm, 99.99+%

Nickel, wire reel, 10m, diameter 0.25mm, hard, 99.98%

Nickel, foil, 4mm disks, thickness 0.009mm, 99.95%

Nickel, foil, 0.5m coil, thickness 0.0075mm, 99.9%

Nickel, wire reel, 100m, diameter 0.25mm, hard, 99.98%

Nickel, wire reel, 0.2m, diameter 0.5mm, as drawn, 99.99+%

Nickel, foil, 10mm disks, thickness 0.003mm, 99.95%

Nickel, foil, 2m coil, thickness 0.3mm, annealed, 99%

Nickel, foil, 50x50mm, thickness 1.0mm, annealed, 99.98%

Nickel, tube, 500mm, outside diameter 3.6mm, inside diameter 3.5mm, wall thickness 0.05mm, hard, 99.5%

Nickel, foil, 50x50mm, thickness 0.125mm, annealed, 99%

Nickel, rod, 1000mm, diameter 2.0mm, annealed, 99%

Nickel, wire reel, 1m, diameter 0.25mm, as drawn, 99.99+%

Nickel, foil, 150x150mm, thickness 1.0mm, annealed, 99%

Nickel, foil, 4mm disks, thickness 0.02mm, 99.9%