Stereospecific Ni-catalyzed cross-coupling of potassium alkenyltrifluoroborates with alkyl halides.

Organic letters (2014-03-29)
Gary A Molander, O Andreea Argintaru
RESUMO

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.

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Raney®-Nickel, W.R. Grace and Co. Raney®2800, slurry, in H2O, active catalyst
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Nickel, powder, <50 μm, 99.7% trace metals basis
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Nickel, nanopowder, <100 nm avg. part. size, ≥99% trace metals basis
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Nickel, powder, <150 μm, 99.99% trace metals basis
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Nickel, foil, thickness 0.125 mm, ≥99.9%
Nickel, foam, 150x150mm, thickness 1.6mm, bulk density 0.45g/cm3, porosity 95%, 95%
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Nickel, powder, <1 μm, 99.8% trace metals basis
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Nickel, foil, thickness 0.5 mm, 99.98% trace metals basis
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Raney®-Nickel, W.R. Grace and Co. Raney®2400, slurry, in H2O, active catalyst
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Nickel, wire, diam. 0.5 mm, ≥99.9% 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. 0.25 mm, ≥99.9%
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Nickel, rod, diam. 6.35 mm, ≥99.99% trace metals basis
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Nickel, wire, diam. 0.5 mm, ≥99.99% trace metals basis
Nickel, tube, 500mm, outside diameter 1.8mm, inside diameter 1.6mm, wall thickness 0.1mm, hard, 99.5%
Nickel, wire reel, 20m, diameter 0.025mm, as drawn, 99.98%
Nickel, wire reel, 1m, diameter 1.0mm, as drawn, 99%
Nickel, mesh, 100x250mm, nominal aperture 0.73mm, wire diameter 0.25mm, 26x26 wires/inch, open area 55%, plain weave mesh, 99%
Nickel, sphere, 100pcs, diameter 1.0mm, precision sphere grade 200, 99%
Nickel, foil, 50x50mm, thickness 0.30mm, as rolled, 99.98%
Nickel, wire reel, 5m, diameter 1.0mm, hard, 99.98%
Nickel, wire reel, 1m, diameter 0.75mm, as drawn, 99%
Nickel, rod, 100mm, diameter 12.7mm, 99.98%
Nickel, sphere, 200pcs, diameter 3.0mm, precision sphere grade 200, 99%
Nickel, foil, light tested, 100x100mm, thickness 0.015mm, 99.9%
Nickel, foil, 10mm disks, thickness 0.15mm, annealed, 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%

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