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

357634

Sigma-Aldrich

Nickel, wire, diam. 0.25 mm, ≥99.9%

510068

Sigma-Aldrich

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

203904

Sigma-Aldrich

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

268259

Sigma-Aldrich

Nickel, foil, thickness 0.125 mm, ≥99.9%

268283

Sigma-Aldrich

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

267007

Sigma-Aldrich

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

267058

Sigma-Aldrich

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221678

Sigma-Aldrich

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

510033

Sigma-Aldrich

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

GF32263354

Nickel, foil, 25x25mm, thickness 0.25mm, as rolled, 99.99+%

GF26283179

Nickel, foil, 0.5m coil, thickness 0.3mm, annealed, 99%

GF47006243

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Nickel, foil, 10m coil, thickness 0.3mm, coil width 1mm, as rolled, 99%

GF91050140

Nickel, wire reel, 100m, diameter 0.125mm, hard, 99.98%

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Nickel, foil, 50x50mm, thickness 0.25mm, as rolled, 99.999%

GF64268118

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Nickel, foil, 10m coil, thickness 0.20mm, coil width 1mm, annealed, 99%

GF34426470

Nickel, tube, 500mm, outside diameter 5.9mm, inside diameter 5.65mm, wall thickness 0.125mm, hard, 99.5%

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Nickel, foil, 50x50mm, thickness 0.25mm, annealed, 99.98%

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Nickel, foil, 50x50mm, thickness 0.125mm, annealed, 99.98%

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