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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, 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

Sigma-Aldrich

Raney^®-Nickel, W.R. Grace and Co. Raney^® 3202, slurry, in H₂O, active catalyst

Sigma-Aldrich

Raney^®-Nickel, W.R. Grace and Co. Raney^® 4200, slurry, in H₂O, active catalyst

Sigma-Aldrich

Nickel, powder, <1 μm, 99.8% trace metals basis

Sigma-Aldrich

Nickel, wire, diam. 0.5 mm, ≥99.99% trace metals basis

Sigma-Aldrich

Nickel, foil, thickness 0.25 mm, 99.995% trace metals basis

Sigma-Aldrich

Nickel, foil, thickness 0.125 mm, ≥99.9%

Sigma-Aldrich

Nickel, wire, diam. 0.25 mm, ≥99.9%

Nickel, wire reel, 10m, diameter 0.25mm, as drawn, 99.99+%

Nickel, rod, 500mm, diameter 3.0mm, 99%

Nickel, rod, 100mm, diameter 5.0mm, 99.99+%

Nickel, rod, 100mm, diameter 2.0mm, 99.99+%

Nickel, rod, 100mm, diameter 2.0mm, annealed, 99%

Nickel, rod, 200mm, diameter 2.0mm, 99.99+%

Nickel, rod, 200mm, diameter 3.0mm, 99%

Nickel, sphere, 100pcs, diameter 1.0mm, precision sphere grade 200, 99%

Nickel, rod, 100mm, diameter 25.4mm, 99.98%

Nickel, rod, 100mm, diameter 40mm, 99%

Nickel, rod, 100mm, diameter 3.0mm, 99%

Nickel, foil, light tested, 25x25mm, thickness 0.0125mm, 99.9%

Nickel, foil, light tested, 50x50mm, thickness 0.05mm, as rolled, 99.98%

Nickel, foil, light tested, 50x50mm, thickness 0.02mm, 99.9%

Nickel, foil, light tested, 300x300mm, thickness 0.025mm, annealed, 99%

Nickel, rod, 100mm, diameter 1.5mm, 99.99+%

Nickel, foil, 25x25mm, thickness 0.1mm, annealed, 99%

Nickel, pellets, 100g, max. size 10mm, 99.99+%

Nickel, foil, light tested, 100x100mm, thickness 0.015mm, 99.9%

Nickel, foil, 2m coil, thickness 0.01mm, 99.95%