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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

Raney^®-Nickel, W.R. Grace and Co. Raney^® 2400, slurry, in H₂O, active catalyst

Nickel, insulated wire, 50m, conductor diameter 0.025mm, insulation thickness 0.0035mm, polyimide insulation

Sigma-Aldrich

Nickel, foil, thickness 0.125 mm, ≥99.9%

Nickel, wire reel, 200m, diameter 0.125mm, annealed, 99.98%

Sigma-Aldrich

Nickel, foil, thickness 0.25 mm, 99.995% trace metals basis

Nickel, foil, light tested, 25x25mm, thickness 0.015mm, 99.9%

Nickel, wire reel, 50m, diameter 1.0mm, as drawn, 99%

Nickel, rod, 100mm, diameter 2.0mm, annealed, 99%

Nickel, wire reel, 1m, diameter 2.0mm, hard, 99.98%

Nickel, rod, 100mm, diameter 40mm, 99%

Nickel, pellets, 100g, max. size 10mm, 99.99+%

Nickel, foil, light tested, 100x100mm, thickness 0.015mm, 99.9%

Sigma-Aldrich

Nickel, sputtering target, diam. × thickness 2.00 in. × 0.25 in., 99.95% trace metals basis

Sigma-Aldrich

Nickel, wire, diam. 0.25 mm, ≥99.9%

Nickel, rod, 500mm, diameter 12.7mm, 99.98%

Nickel, foil, 25mm disks, thickness 0.05mm, as rolled, 99.98%

Nickel, rod, 200mm, diameter 3.0mm, 99%

Nickel, tube, 1000mm, outside diameter 2.4mm, inside diameter 2.248mm, wall thickness 0.076mm, hard, 99.5%

Nickel, foil, 50mm disks, thickness 0.003mm, 99.95%

Nickel, foil, 15mm disks, thickness 0.125mm, annealed, 99%

Nickel, foil, 4mm disks, thickness 0.5mm, as rolled, 100%

Nickel, tube, 100mm, outside diameter 1.8mm, inside diameter 1.6mm, wall thickness 0.1mm, hard, 99.5%

Nickel, foil, 1m coil, thickness 0.025mm, coil width 600mm, as rolled, 99%

Nickel, foil, 15mm disks, thickness 0.075mm, as rolled, 99.98%

Nickel, rod, 500mm, diameter 3.0mm, 99%

Nickel, foil, 50mm disks, thickness 0.5mm, as rolled, 99.99+%

Nickel, tube, 200mm, outside diameter 0.35mm, inside diameter 0.3mm, wall thickness 0.025mm, hard, 99.5%

Nickel, foil, 50mm disks, thickness 0.0075mm, 99.95%

Nickel, rod, 500mm, diameter 1.5mm, 99.99+%

Nickel, rod, 100mm, diameter 5.0mm, 99.99+%