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

267007

Sigma-Aldrich

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

267058

Sigma-Aldrich

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

268283

Sigma-Aldrich

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

357634

Sigma-Aldrich

Nickel, wire, diam. 0.25 mm, ≥99.9%

268259

Sigma-Aldrich

Nickel, foil, thickness 0.125 mm, ≥99.9%

GF45193697

Nickel, rod, 100mm, diameter 2.0mm, annealed, 99%

GF61468421

Nickel, foil, 10mm disks, thickness 0.125mm, as rolled, 99.99+%

GF20399159

Nickel, tube, 100mm, outside diameter 1.5mm, inside diameter 1.4mm, wall thickness 0.05mm, hard, 99.5%

GF85665842

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

GF08912831

Nickel, foil, 10mm disks, thickness 0.15mm, annealed, 99%

GF01381407

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

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Nickel, rod, 500mm, diameter 12.7mm, 99.98%

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

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Nickel, foil, 10mm disks, thickness 0.50mm, annealed, 99%

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Nickel, rod, 200mm, diameter 3.0mm, 99%

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Nickel, rod, 100mm, diameter 25.4mm, 99.98%

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Nickel, foil, 10mm disks, thickness 0.5mm, annealed, 99.98%

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Nickel, rod, 200mm, diameter 3.3mm, 99.99+%

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Nickel, tube, 100mm, outside diameter 2.0mm, inside diameter 1.8mm, wall thickness 0.1mm, hard, 99.5%

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Nickel, tube, 1000mm, outside diameter 7.11mm, inside diameter 6.57mm, wall thickness 0.27mm, hard, 99.5%

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Nickel, tube, 1000mm, outside diameter 2.0mm, inside diameter 1.6mm, wall thickness 0.2mm, hard, 99.5%

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Nickel, rod, 500mm, diameter 2.0mm, annealed, 99%

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Nickel, rod, 200mm, diameter 12.0mm, 99%

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