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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, wire, diam. 0.5 mm, ≥99.99% trace metals basis
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
Raney®-Nickel, W.R. Grace and Co. Raney® 2400, slurry, in H2O, active catalyst
Nickel, tube, 200mm, outside diameter 0.8mm, inside diameter 0.3mm, wall thickness 0.25mm, as drawn, 99.5%
Nickel, wire reel, 50m, diameter 0.25mm, as drawn, 99%
Nickel, wire reel, 250m, diameter 0.125mm, as drawn, 99%
Nickel, tube, 200mm, outside diameter 1.3mm, inside diameter 1.1mm, wall thickness 0.1mm, hard, 99.5%
Nickel, foil, 25mm disks, thickness 0.05mm, as rolled, 99.98%
Nickel, foil, 1m coil, thickness 0.03mm, 99.9%
Nickel, tube, 1000mm, outside diameter 3.25mm, inside diameter 3.05mm, wall thickness 0.1mm, hard, 99.5%
Nickel, tube, 1000mm, outside diameter 0.762mm, inside diameter 0.204mm, wall thickness 0.279mm, hard, 99.5%
Nickel, foil, 15mm disks, thickness 0.5mm, annealed, 99.98%
Nickel, tube, 200mm, outside diameter 2.0mm, inside diameter 1.6mm, wall thickness 0.2mm, hard, 99.5%
Nickel, wire reel, 5m, diameter 0.025mm, as drawn, 99.6+%
Nickel, wire reel, 500m, diameter 0.4mm, as drawn, 99%
Nickel, wire reel, 20m, diameter 0.125mm, hard, 99.98%
Nickel, tube, 500mm, outside diameter 0.8mm, inside diameter 0.3mm, wall thickness 0.25mm, as drawn, 99.5%
Nickel, tube, 1000mm, outside diameter 1.5mm, inside diameter 1.4mm, wall thickness 0.05mm, hard, 99.5%
Nickel, foil, 1m coil, thickness 0.0125mm, 99.9%
Nickel, wire reel, 1m, diameter 1.0mm, hard, 99.98%
Nickel, tube, 200mm, outside diameter 0.8mm, inside diameter 0.5mm, wall thickness 0.15mm, as drawn, 99.5%
Nickel, foil, 25mm disks, thickness 0.03mm, 99.9%
Nickel, foil, 10m coil, thickness 0.3mm, coil width 1mm, annealed, 99%
Nickel, foil, 150x150mm, thickness 0.25mm, annealed, 99.98%
Nickel, wire reel, 100m, diameter 0.5mm, annealed, 99%
Nickel, foil, 4mm disks, thickness 0.0125mm, 99.99+%
Nickel, wire reel, 0.2m, diameter 1.0mm, as drawn, 99.99+%
Nickel, foil, 0.5m coil, thickness 0.25mm, annealed, 99%
Nickel, wire reel, 1m, diameter 0.5mm, as drawn, 99.99+%