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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

ABSTRAKT

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.

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Raney^®-Nickel, W.R. Grace and Co. Raney^® 2400, slurry, in H₂O, active catalyst

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

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Nickel, foil, thickness 0.125 mm, ≥99.9%

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

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

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

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

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

Nickel, broken cathode squares, 500g, max. size 50mm, 99.8%

Sigma-Aldrich

Nickel, wire, diam. 0.25 mm, ≥99.9%

Nickel, wire reel, 50m, diameter 1.0mm, as drawn, 99%

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

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

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

Nickel, rod, 500mm, diameter 12.7mm, 99.98%

Nickel, wire reel, 5m, diameter 0.5mm, as drawn, 99.99+%

Nickel, wire reel, 1m, diameter 2.0mm, hard, 99.98%

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

Nickel, insulated wire, 50m, conductor diameter 0.025mm, insulation thickness 0.0035mm, polyimide insulation

Nickel, wire reel, 200m, diameter 0.125mm, annealed, 99.98%

Nickel, foil, light tested, 25x25mm, thickness 0.015mm, 99.9%

Nickel, foil, 25mm disks, thickness 0.05mm, as rolled, 99.98%

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

Nickel, tube, 1000mm, outside diameter 2.4mm, inside diameter 2.248mm, wall thickness 0.076mm, hard, 99.5%

Nickel, foil, 15mm disks, thickness 0.125mm, annealed, 99%

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

Nickel, tube, 100mm, outside diameter 1.8mm, inside diameter 1.6mm, wall thickness 0.1mm, hard, 99.5%

Nickel, foil, 15mm disks, thickness 0.075mm, as rolled, 99.98%

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