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

510068

Sigma-Aldrich

Raney^®-Nickel, W.R. Grace and Co. Raney^® 3202, slurry, in H₂O, active catalyst

510041

Sigma-Aldrich

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510033

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203904

Sigma-Aldrich

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

267058

Sigma-Aldrich

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268259

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268283

Sigma-Aldrich

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357634

Sigma-Aldrich

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221678

Sigma-Aldrich

Raney^®-Nickel, W.R. Grace and Co. Raney^® 2800, slurry, in H₂O, active catalyst

267007

Sigma-Aldrich

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

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GF67542194

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GF20349435

Nickel, foil, not light tested, 50x50mm, thickness 0.005mm, as rolled, 99.9%

GF05348213

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Nickel, foil, 300x300mm, thickness 2.0mm, annealed, 99%

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Nickel, foil, not light tested, 100x100mm, thickness 0.01mm, 99.95%

GF22505284

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GF21421268

Nickel, mesh, 60x60mm, nominal aperture 0.43mm, thickness 0.004mm, wire diameter 0.067mm, 51 wires/inch, open area 75%, electro-formed mesh, 99.9%

GF08322858

Nickel, foil, 2m coil, thickness 0.05mm, as rolled, 99.98%

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