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

RÉSUMÉ

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.

MATÉRIAUX

Référence du produit

Marque

Description du produit

221678

Sigma-Aldrich

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

577995

Sigma-Aldrich

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

510033

Sigma-Aldrich

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

266981

Sigma-Aldrich

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

203904

Sigma-Aldrich

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

268259

Sigma-Aldrich

Nickel, foil, thickness 0.125 mm, ≥99.9%

357634

Sigma-Aldrich

Nickel, wire, diam. 0.25 mm, ≥99.9%

268283

Sigma-Aldrich

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

357553

Sigma-Aldrich

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

267007

Sigma-Aldrich

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

GF56791378

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

357588

Sigma-Aldrich

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

267074

Sigma-Aldrich

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

GF86063654

Nickel, foil, 100x100mm, thickness 1.6mm, 99%

267058

Sigma-Aldrich

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

767484

Sigma-Aldrich

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

GF04391591

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

GF21346848

Nickel, rod, 100mm, diameter 1.5mm, 99.99+%

357626

Sigma-Aldrich

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

GF17897596

Nickel, pellets, 100g, max. size 5mm, 99.99+%

GF18587975

Nickel, sphere, 100pcs, diameter 1.0mm, precision sphere grade 200, 99%

GF88290625

Nickel, foil, 100x100mm, thickness 0.25mm, annealed, 99%

GF57012421

Nickel, foil, 50x50mm, thickness 0.3mm, as rolled, 99.999%

GF37939506

Nickel, mesh, 30x30mm, nominal aperture 0.34mm, thickness 0.025mm, wire diameter 0.041mm, 70 wires/inch, open area 80%, electro-formed mesh, 99.9%

GF60569455

Nickel, foil, 100x100mm, thickness 0.1mm, annealed, 99%

GF56481969

Nickel, pellets, 20g, max. size 5mm, 99.99+%

GF27854196

Nickel, foil, 50x50mm, thickness 1.6mm, 99%

GF77657888

Nickel, mesh, 120x120mm, nominal aperture 0.43mm, thickness 0.004mm, wire diameter 0.067mm, 51 wires/inch, open area 75%, electro-formed mesh, 99.9%

GF89678570

Nickel, wire reel, 100m, diameter 0.025mm, as drawn, 99.98%

GF38044627

Nickel, foil, 300x300mm, thickness 0.125mm, annealed, 99%