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

357626

Sigma-Aldrich

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

577995

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

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GF87509997

Nickel, foil, 4mm disks, thickness 0.5mm, annealed, 99.98%

357553

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

267074

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

266981

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

357588

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