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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
Sigma-Aldrich
Raney®-Nickel, W.R. Grace and Co. Raney® 4200, slurry, in H2O, active catalyst
Sigma-Aldrich
Raney®-Nickel, W.R. Grace and Co. Raney® 3202, slurry, in H2O, active catalyst
Sigma-Aldrich
Nickel, powder, <150 μm, 99.99% trace metals basis
Sigma-Aldrich
Raney®-Nickel, W.R. Grace and Co. Raney® 2800, slurry, in H2O, active catalyst
Sigma-Aldrich
Nickel, foil, thickness 0.125 mm, ≥99.9%
Sigma-Aldrich
Nickel, wire, diam. 0.5 mm, ≥99.99% trace metals basis
Sigma-Aldrich
Nickel, powder, <1 μm, 99.8% trace metals basis
Sigma-Aldrich
Nickel, wire, diam. 0.25 mm, ≥99.9%
Sigma-Aldrich
Nickel, foil, thickness 0.25 mm, 99.995% trace metals basis
Nickel, wire reel, 10m, diameter 0.05mm, as drawn, 99.99+%
Nickel, foil, 150x150mm, thickness 2.0mm, annealed, 99%
Nickel, foil, not light tested, 50x50mm, thickness 0.00075mm, temporary acrylic support, 99.95%
Nickel, wire reel, 0.5m, diameter 0.25mm, as drawn, 99.99+%
Nickel, foil, 2m coil, thickness 0.30mm, as rolled, 99.98%
Nickel, rod, 1000mm, diameter 12.0mm, 99%
Nickel, foil, not light tested, 50x50mm, thickness 0.004mm, hard, 99%
Nickel, rod, 1000mm, diameter 9.5mm, 99%
Nickel, foil, 25x25mm, thickness 0.3mm, as rolled, 99.999%
Nickel, mesh, 60x60mm, nominal aperture 0.43mm, thickness 0.004mm, wire diameter 0.067mm, 51 wires/inch, open area 75%, electro-formed mesh, 99.9%
Nickel, foil, 4mm disks, thickness 0.005mm, as rolled, 99.9%
Nickel, mesh, 100x250mm, nominal aperture 0.73mm, wire diameter 0.25mm, 26x26 wires/inch, open area 55%, plain weave mesh, 99%
Nickel, wire reel, 0.5m, diameter 0.4mm, as drawn, 99.99+%
Nickel, foil, 25x25mm, thickness 0.25mm, as rolled, 99.99+%
Nickel, foil, 0.5m coil, thickness 0.3mm, annealed, 99%
Nickel, pellets, 100g, max. size 5mm, 99.99+%
Nickel, foil, 4mm disks, thickness 0.0025mm, 99.95%
Nickel, foil, 0.5m coil, thickness 0.003mm, 99.95%
Nickel, foil, 4mm disks, thickness 0.0075mm, 99.9%
Nickel, foil, 50x50mm, thickness 0.25mm, as rolled, 99.999%