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

267058

Sigma-Aldrich

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

203904

Sigma-Aldrich

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

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

GF97647845

Nickel, tube, 200mm, outside diameter 0.8mm, inside diameter 0.3mm, wall thickness 0.25mm, as drawn, 99.5%

GF10884764

Nickel, wire reel, 50m, diameter 0.25mm, as drawn, 99%

GF64122094

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

GF18961960

Nickel, tube, 200mm, outside diameter 1.3mm, inside diameter 1.1mm, wall thickness 0.1mm, hard, 99.5%

GF32802511

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

GF10592502

Nickel, foil, 1m coil, thickness 0.03mm, 99.9%

GF19259365

Nickel, tube, 1000mm, outside diameter 3.25mm, inside diameter 3.05mm, wall thickness 0.1mm, hard, 99.5%

GF18389863

Nickel, tube, 1000mm, outside diameter 0.762mm, inside diameter 0.204mm, wall thickness 0.279mm, hard, 99.5%

GF51999373

Nickel, foil, 15mm disks, thickness 0.5mm, annealed, 99.98%

GF57539201

Nickel, tube, 200mm, outside diameter 2.0mm, inside diameter 1.6mm, wall thickness 0.2mm, hard, 99.5%

GF11019697

Nickel, wire reel, 5m, diameter 0.025mm, as drawn, 99.6+%

GF27783298

Nickel, wire reel, 500m, diameter 0.4mm, as drawn, 99%

GF38092226

Nickel, wire reel, 20m, diameter 0.125mm, hard, 99.98%

GF05980754

Nickel, tube, 500mm, outside diameter 0.8mm, inside diameter 0.3mm, wall thickness 0.25mm, as drawn, 99.5%

GF54633630

Nickel, tube, 1000mm, outside diameter 1.5mm, inside diameter 1.4mm, wall thickness 0.05mm, hard, 99.5%

GF21689129

Nickel, foil, 1m coil, thickness 0.0125mm, 99.9%

GF45846456

Nickel, wire reel, 1m, diameter 1.0mm, hard, 99.98%

GF41664753

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

GF59353847

Nickel, foil, 25mm disks, thickness 0.03mm, 99.9%

GF65651564

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

GF19140342

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

GF17533997

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

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

GF00207638

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

GF19621144

Nickel, foil, 0.5m coil, thickness 0.25mm, annealed, 99%

GF77403898

Nickel, wire reel, 1m, diameter 0.5mm, as drawn, 99.99+%