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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

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

Sigma-Aldrich

Nickel, foil, thickness 0.125 mm, ≥99.9%

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Nickel, wire, diam. 0.25 mm, ≥99.9%

Nickel, foil, 4mm disks, thickness 0.125mm, annealed, 99.98%

Nickel, foil, 4mm disks, thickness 0.5mm, as rolled, 100%

Nickel, foil, 50mm disks, thickness 0.05mm, as rolled, 99.98%

Nickel, foil, 5m coil, thickness 0.125mm, annealed, 99.98%

Nickel, foil, 50mm disks, thickness 0.25mm, annealed, 99.98%

Nickel, foil, 4mm disks, thickness 0.3mm, annealed, 99%

Nickel, foil, 4mm disks, thickness 0.5mm, as rolled, 99.99+%

Nickel, foil, 5m coil, thickness 0.0075mm, 99.95%

Nickel, foil, 4mm disks, thickness 0.25mm, annealed, 99.98%

Nickel, foil, 5m coil, thickness 0.125mm, coil width 1mm, as rolled, 99%

Nickel, foil, 4mm disks, thickness 0.075mm, as rolled, 99.98%

Nickel, foil, 50mm disks, thickness 0.0125mm, annealed, 99%

Nickel, foil, 10mm disks, thickness 0.008mm, 99.95%

Nickel, wire reel, 1m, diameter 0.75mm, as drawn, 99.99+%

Nickel, wire reel, 10m, diameter 0.05mm, as drawn, 99%

Nickel, foil, 4mm disks, thickness 0.05mm, 99.9%

Nickel, wire reel, 10m, diameter 0.5mm, hard, 99.98%

Nickel, wire reel, 100m, diameter 0.5mm, hard, 99.98%

Nickel, foil, 4mm disks, thickness 0.015mm, 99.9%

Nickel, foil, 0.5m coil, thickness 0.015mm, 99.9%

Nickel, foil, 4mm disks, thickness 0.05mm, annealed, 99%

Nickel, wire reel, 10m, diameter 0.75mm, as drawn, 99%