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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, foil, thickness 0.1 mm, 99.98% trace metals basis

Sigma-Aldrich

Nickel, powder, <50 μm, 99.7% trace metals basis

Sigma-Aldrich

Nickel, nanopowder, <100 nm avg. part. size, ≥99% 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, wire reel, 5m, diameter 0.5mm, hard, 99.98%

Nickel, foil, 25mm disks, thickness 0.01mm, 99.95%

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

Nickel, tube, 1000mm, outside diameter 4.5mm, inside diameter 3.154mm, wall thickness 0.673mm, hard, 99.5%

Nickel, foil, 1m coil, thickness 0.3mm, coil width 1mm, annealed, 99%

Nickel, tube, 200mm, outside diameter 7.11mm, inside diameter 6.57mm, wall thickness 0.27mm, hard, 99.5%

Nickel, tube, 1000mm, outside diameter 0.65mm, inside diameter 0.384mm, wall thickness 0.133mm, as drawn, 99.5%

Nickel, wire reel, 500m, diameter 0.25mm, hard, 99.98%

Nickel, foil, 6mm disks, thickness 0.005mm, as rolled, 99.9%

Nickel, foil, 25mm disks, thickness 0.003mm, 99.95%

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

Nickel, foil, 1m coil, thickness 0.075mm, as rolled, 99.98%

Nickel, foil, 15mm disks, thickness 0.30mm, as rolled, 99.98%

Nickel, rod, 50mm, diameter 10.0mm, 99.99+%

Nickel, wire reel, 1m, diameter 1.0mm, as drawn, 99%

Nickel, foil, 1m coil, thickness 0.1mm, annealed, 99%

Nickel, foil, 8mm disks, thickness 0.0025mm, 99.95%

Nickel, rod, 50mm, diameter 40mm, 99%

Nickel, foil, 15mm disks, thickness 0.5mm, as rolled, 99.99+%

Nickel, tube, 200mm, outside diameter 4.5mm, inside diameter 3.154mm, wall thickness 0.673mm, hard, 99.5%

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

Nickel, foil, 1m coil, thickness 0.3mm, coil width 1mm, as rolled, 99%

Nickel, foil, 1m coil, thickness 0.0075mm, 99.95%

Nickel, foil, 25mm disks, thickness 0.125mm, annealed, 99.98%