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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® 2800, slurry, in H2O, active catalyst
Sigma-Aldrich
Nickel, nanopowder, <100 nm avg. part. size, ≥99% trace metals basis
Sigma-Aldrich
Nickel, powder, <150 μm, 99.99% trace metals basis
Sigma-Aldrich
Nickel, foil, thickness 0.125 mm, ≥99.9%
Sigma-Aldrich
Raney®-Nickel, W.R. Grace and Co. Raney® 2400, slurry, in H2O, active catalyst
Sigma-Aldrich
Nickel, wire, diam. 0.25 mm, ≥99.9%
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Nickel, foil, thickness 0.5 mm, 99.98% trace metals basis
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Nickel, foil, thickness 0.1 mm, 99.98% trace metals basis
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Nickel, wire, diam. 0.5 mm, ≥99.9% trace metals basis
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Nickel, wire, diam. 0.5 mm, ≥99.99% trace metals basis
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Nickel, foil, thickness 0.25 mm, 99.995% trace metals basis
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Nickel, rod, diam. 6.35 mm, ≥99.99% trace metals basis
Nickel, mesh, 100x250mm, nominal aperture 0.73mm, wire diameter 0.25mm, 26x26 wires/inch, open area 55%, plain weave mesh, 99%
Nickel, wire reel, 20m, diameter 0.025mm, as drawn, 99.98%
Nickel, wire reel, 10m, diameter 0.01mm, as drawn, 99.98%
Nickel, rod, 100mm, diameter 16mm, 99.99+%
Nickel, foil, not light tested, 100x100mm, thickness 0.01mm, 99.95%
Nickel, wire reel, 20m, diameter 0.125mm, hard, 99.98%
Nickel, rod, 100mm, diameter 3.0mm, 99%
Nickel, wire reel, 1m, diameter 1.0mm, hard, 99.98%
Nickel, broken cathode squares, 1000g, max. size 50mm, 99.8%
Nickel, tube, 1000mm, outside diameter 6.5mm, inside diameter 5.5mm, wall thickness 0.5mm, hard, 99.5%
Nickel, foil, 50mm disks, thickness 0.05mm, annealed, 99%
Nickel, wire reel, 20m, diameter 0.5mm, as drawn, 99%
Nickel, foil, 4mm disks, thickness 0.075mm, annealed, 99%
Nickel, foil, 4mm disks, thickness 0.075mm, as rolled, 99.98%
Nickel, foil, 4mm disks, thickness 0.125mm, annealed, 99%
Nickel, foil, 4mm disks, thickness 0.125mm, annealed, 99.98%
Nickel, foil, 4mm disks, thickness 0.125mm, as rolled, 100%
Nickel, foil, 4mm disks, thickness 0.125mm, as rolled, 99.99+%