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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

Nickel, foil, light tested, 100x100mm, thickness 0.007mm, 99.95%

Nickel, foil, not light tested, 100x100mm, thickness 0.002mm, 99.95%

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

Nickel, foil, 50x50mm, thickness 0.5mm, as rolled, 99.99+%

Nickel, foil, 300x300mm, thickness 0.125mm, annealed, 99%

Nickel, foil, 0.5m coil, thickness 0.025mm, annealed, 99%

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

Nickel, foil, light tested, 50x50mm, thickness 0.05mm, 99.9%

Nickel, mesh, 30x30mm, nominal aperture 0.34mm, thickness 0.025mm, wire diameter 0.041mm, 70 wires/inch, open area 80%, electro-formed mesh, 99.9%

Nickel, foil, light tested, 300x300mm, thickness 0.03mm, 99.9%

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

Nickel, foil, 50x50mm, thickness 0.25mm, annealed, 99%

Nickel, foil, 25x25mm, thickness 0.5mm, as rolled, 99.99+%

Nickel, foil, 25x25mm, thickness 1.0mm, annealed, 99.98%

Nickel, foil, 25x25mm, thickness 0.125mm, annealed, 99%

Nickel, foil, 0.5m coil, thickness 0.075mm, as rolled, 99.98%

Nickel, wire reel, 10m, diameter 0.4mm, as drawn, 99%

Nickel, wire reel, 10m, diameter 0.25mm, annealed, 99%

Nickel, foil, 4mm disks, thickness 0.025mm, as rolled, 100%

Nickel, mesh, 130x130mm, nominal aperture 0.34mm, thickness 0.025mm, wire diameter 0.041mm, 70 wires/inch, open area 80%, electro-formed mesh, 99.9%

Nickel, foil, 0.5m coil, thickness 0.025mm, coil width 600mm, as rolled, 99%

Nickel, foil, 4mm disks, thickness 0.025mm, 99.9%

Nickel, wire reel, 0.5m, diameter 1.0mm, as drawn, 99.99+%

Nickel, foil, 2m coil, thickness 0.50mm, annealed, 99%

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

Nickel, foil, 50x50mm, thickness 1.0mm, as rolled, 99.99+%

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

Nickel, foil, 25x25mm, thickness 0.25mm, as rolled, 99.999%

Nickel, foil, 0.5m coil, thickness 1.0mm, annealed, 99%

Nickel, rod, 100mm, diameter 10.0mm, 99.99+%