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

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

357553

Sigma-Aldrich

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

357588

Sigma-Aldrich

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

357626

Sigma-Aldrich

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

266981

Sigma-Aldrich

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

GF49327892

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GF50441228

Nickel, foil, not light tested, 50x50mm, thickness 0.0025mm, 99.95%

GF82377816

Nickel, foil, 50x50mm, thickness 0.125mm, as rolled, 99.999%

GF69666328

Nickel, rod, 1000mm, diameter 6.35mm, 99%

GF07787986

Nickel, foil, 25x25mm, thickness 0.3mm, annealed, 99%

GF10370618

Nickel, mesh, 30x30mm, nominal aperture 0.04mm, thickness 0.004mm, wire diameter 0.011mm, 500 wires/inch, open area 60%, electro-formed mesh, 99.9%

GF57012421

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

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Nickel, foil, 25x25mm, thickness 2.0mm, annealed, 99%

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Nickel, foil, 25x25mm, thickness 0.125mm, as rolled, 99.999%

GF71874388

Nickel, foil, 2m coil, thickness 0.025mm, coil width 600mm, as rolled, 99%

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Nickel, foil, 50x50mm, thickness 1.0mm, as rolled, 99.999%

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Nickel, mesh, 240x240mm, nominal aperture 0.43mm, thickness 0.004mm, wire diameter 0.067mm, 51 wires/inch, open area 75%, electro-formed mesh, 99.9%

GF33286282

Nickel, foil, 50x50mm, thickness 2.0mm, annealed, 99%

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Nickel, foil, 150x300mm, thickness 0.25mm, annealed, 99.98%

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Nickel, microfoil, disks, 25mm, thinness 1.0μm, specific density 895.8μg/cm², permanent mylar 3.5μm support, 99.99+%

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Nickel, wire reel, 10m, diameter 0.125mm, hard, 99.98%

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Nickel, foil, 150x300mm, thickness 0.5mm, annealed, 99.98%

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Nickel, mesh, 30x30mm, nominal aperture 0.43mm, thickness 0.004mm, wire diameter 0.067mm, 51 wires/inch, open area 75%, electro-formed mesh, 99.9%

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Nickel, foil, not light tested, 50x50mm, thickness 0.007mm, 99.95%