Skip to Content

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, foil, thickness 0.1 mm, 99.98% trace metals basis

Sigma-Aldrich

Nickel, wire, diam. 0.5 mm, ≥99.9% trace metals basis

Sigma-Aldrich

Nickel, nanopowder, <100 nm avg. part. size, ≥99% trace metals basis

Sigma-Aldrich

Nickel, foil, thickness 0.5 mm, 99.98% trace metals basis

Sigma-Aldrich

Nickel, powder, <50 μm, 99.7% trace metals basis

Sigma-Aldrich

Nickel, rod, diam. 6.35 mm, ≥99.99% trace metals basis

Nickel, wire reel, 1m, diameter 1.0mm, as drawn, 99%

Sigma-Aldrich

Nickel, sputtering target, diam. × thickness 2.00 in. × 0.25 in., 99.95% trace metals basis

Sigma-Aldrich

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

Sigma-Aldrich

Nickel, powder, <150 μm, 99.99% trace metals basis

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, wire, diam. 0.25 mm, ≥99.9%

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

Raney^®-Nickel, W.R. Grace and Co. Raney^® 2800, slurry, in H₂O, active catalyst

Nickel, broken cathode squares, 1000g, max. size 50mm, 99.8%

Nickel, foam, 300x300mm, thickness 1.6mm, bulk density 0.45g/cm³, porosity 95%, 95%