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

266981

Sigma-Aldrich

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

357553

Sigma-Aldrich

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

357626

Sigma-Aldrich

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

577995

Sigma-Aldrich

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

267074

Sigma-Aldrich

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

GF88726168

Nickel, foil, light tested, 25x25mm, thickness 0.009mm, 99.95%

GF49268526

Nickel, tube, 5mm, outside diameter 0.8mm, inside diameter 0.5mm, wall thickness 0.15mm, hard, 99.5%

GF81790690

Nickel, foil, 10mm disks, thickness 0.015mm, 99.9%

GF64774345

Nickel, foil, 10m coil, thickness 0.125mm, coil width 50mm, annealed, 99%

GF85861042

Nickel, foil, 0.5m coil, thickness 0.125mm, annealed, 99%

GF98554078

Nickel, tube, 500mm, outside diameter 3.25mm, inside diameter 3.05mm, wall thickness 0.1mm, hard, 99.5%

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Nickel, foil, 10mm disks, thickness 0.05mm, annealed, 99%

GF03085321

Nickel, foil, 10mm disks, thickness 0.005mm, as rolled, 99.9%

GF16803075

Nickel, foil, 2m coil, thickness 0.125mm, annealed, 99.98%

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Nickel, foil, 2m coil, thickness 0.3mm, annealed, 99%

GF51323093

Nickel, tube, 500mm, outside diameter 3.6mm, inside diameter 3.5mm, wall thickness 0.05mm, hard, 99.5%

GF02127068

Nickel, foil, 10mm disks, thickness 0.0075mm, 99.9%

GF78640768

Nickel, foil, 2m coil, thickness 0.125mm, coil width 50mm, annealed, 99%

GF66058612

Nickel, foil, 10mm disks, thickness 0.025mm, 99.9%

GF35355315

Nickel, wire reel, 0.1m, diameter 0.75mm, as drawn, 99.99+%

GF03677665

Nickel, foil, 2m coil, thickness 0.15mm, annealed, 99%

GF45284081

Nickel, foil, not light tested, 100x100mm, thickness 0.004mm, hard, 99%

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Nickel, foil, 15mm disks, thickness 0.25mm, as rolled, 100%

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Nickel, wire reel, 50m, diameter 0.5mm, as drawn, 99%

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Nickel, tube, 200mm, outside diameter 0.65mm, inside diameter 0.384mm, wall thickness 0.133mm, as drawn, 99.5%