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

268259

Sigma-Aldrich

Nickel, foil, thickness 0.125 mm, ≥99.9%

357634

Sigma-Aldrich

Nickel, wire, diam. 0.25 mm, ≥99.9%

510041

Sigma-Aldrich

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

510068

Sigma-Aldrich

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

510033

Sigma-Aldrich

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

221678

Sigma-Aldrich

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

GF85665842

Nickel, foil, 15mm disks, thickness 0.005mm, as rolled, 99.9%

GF01381407

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

GF41664753

Nickel, tube, 200mm, outside diameter 0.8mm, inside diameter 0.5mm, wall thickness 0.15mm, as drawn, 99.5%

GF56438714

Nickel, tube, 1000mm, outside diameter 2.5mm, inside diameter 2.25mm, wall thickness 0.125mm, hard, 99.5%

GF55104869

Nickel, wire reel, 200m, diameter 0.15mm, as drawn, 99%

GF09806519

Nickel, foil, 10mm disks, thickness 0.125mm, annealed, 99%

GF49702406

Nickel, foil, light tested, 50x50mm, thickness 0.0075mm, 99.95%

GF65651564

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

GF17533997

Nickel, wire reel, 100m, diameter 0.5mm, annealed, 99%

GF19140342

Nickel, foil, 150x150mm, thickness 0.25mm, annealed, 99.98%

GF91050689

Nickel, foil, 4mm disks, thickness 0.0125mm, 99.99+%

GF00207638

Nickel, wire reel, 0.2m, diameter 1.0mm, as drawn, 99.99+%

GF60742548

Nickel, foil, 2m coil, thickness 0.20mm, annealed, 99%

GF31900508

Nickel, foil, 50x50mm, thickness 0.125mm, as rolled, 99.99+%

GF92918616

Nickel, foil, 10mm disks, thickness 0.007mm, 99.95%

GF22505284

Nickel, foil, 150x150mm, thickness 1.6mm, 99%

GF90338508

Nickel, foil, 4mm disks, thickness 0.03mm, 99.9%

GF21073407

Nickel, wire reel, 100m, diameter 0.75mm, as drawn, 99%

GF32662043

Nickel, foil, 50x50mm, thickness 6.35mm, as rolled, 99.99+%

GF00494883

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

GF38418105

Nickel, foil, 4mm disks, thickness 0.05mm, as rolled, 99.98%

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Nickel, wire reel, 100m, diameter 0.25mm, annealed, 99%

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Nickel, microfoil, disks, 10mm, thinness 0.1μm, specific density 93.4μg/cm², permanent mylar 3.5μm support, 99.99+%

GF58401660

Nickel, wire reel, 0.1m, diameter 1.0mm, as drawn, 99.99+%