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

203904

Sigma-Aldrich

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

510033

Sigma-Aldrich

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

267058

Sigma-Aldrich

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

267007

Sigma-Aldrich

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

GF22812634

Nickel, insulated wire, 10m, conductor diameter 0.025mm, insulation thickness 0.0035mm, polyimide insulation

GF34230800

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

GF73290089

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

GF64264181

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

GF10085240

Nickel, pellets, 20g, max. size 10mm, 99.99+%

GF81996014

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

GF20307620

Nickel, broken cathode squares, 100g, max. size 50mm, 99.8%

GF33783677

Nickel, broken cathode squares, 2000g, max. size 50mm, 99.8%

GF95981383

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

GF51346346

Nickel, foil, 100x100mm, thickness 0.125mm, annealed, 99.98%

GF64122094

Nickel, wire reel, 250m, diameter 0.125mm, as drawn, 99%

GF56791378

Nickel, pellets, 100g, max. size 10mm, 99.999%

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Nickel, foil, not light tested, 100x100mm, thickness 0.01mm, 99.95%

GF90261547

Nickel, mesh, 130x130mm, nominal aperture 0.04mm, thickness 0.004mm, wire diameter 0.011mm, 500 wires/inch, open area 60%, electro-formed mesh, 99.9%

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

GF14407927

Nickel, pellets, 100g, max. size 15mm, 99.99+%

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Nickel, foil, not light tested, 50x50mm, thickness 0.005mm, as rolled, 99.9%

GF23635111

Nickel, insulated wire, 5m, conductor diameter 0.025mm, insulation thickness 0.0035mm, polyimide insulation

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Nickel, pellets, 100g, max. size 20mm, 99.99+%

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Nickel, mesh, 60x60mm, nominal aperture 0.43mm, thickness 0.004mm, wire diameter 0.067mm, 51 wires/inch, open area 75%, electro-formed mesh, 99.9%

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Nickel, pellets, 20g, max. size 15mm, 99.99+%

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Nickel, mesh, 100x250mm, nominal aperture 0.73mm, wire diameter 0.25mm, 26x26 wires/inch, open area 55%, plain weave mesh, 99%

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Nickel, mesh, 65x65mm, nominal aperture 0.04mm, thickness 0.004mm, wire diameter 0.011mm, 500 wires/inch, open area 60%, electro-formed mesh, 99.9%

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Nickel, insulated wire, 2m, conductor diameter 0.025mm, insulation thickness 0.0035mm, polyimide insulation

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Nickel, pellets, 50g, max. size 15mm, 99.99+%