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Enantiospecific, nickel-catalyzed cross-couplings of allylic pivalates and arylboroxines.

Enantiospecific, nickel-catalyzed cross-couplings of allylic pivalates and arylboroxines.

Organic letters (2014-06-14)

Harathi D Srinivas, Qi Zhou, Mary P Watson

ABSTRACT

We have developed an enantiospecific, nickel-catalyzed cross-coupling of unsymmetric 1,3-disubstituted allylic pivalates with arylboroxines. The success of this reaction relies on the use of BnPPh2 as a supporting ligand for the nickel(0) catalyst and NaOMe as a base. This method shows excellent functional group tolerance and broad scope in both the allylic pivalate and arylboroxine, enabling the preparation of 1,3-diaryl allylic products in high yields with excellent levels of regioselectivity and stereochemical fidelity.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Nickel, pellets, 50g, max. size 10mm, 99.999%

Sigma-Aldrich

Pivalic acid, 99%

Nickel, foil, 100x100mm, thickness 1.0mm, as rolled, 99.99+%

Sigma-Aldrich

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

Nickel, foil, light tested, 100x100mm, thickness 0.025mm, 99.9%

Nickel, wire reel, 5m, diameter 0.025mm, as drawn, 99.98%

Nickel, foil, 5m coil, thickness 0.05mm, annealed, 99%

Nickel, wire reel, 0.1m, diameter 0.75mm, as drawn, 99.99+%

Nickel, foil, 0.5m coil, thickness 0.025mm, 99.9%

Sigma-Aldrich

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

Nickel, foil, 0.5m coil, thickness 0.0075mm, 99.95%

Nickel, foil, 0.2m coil, thickness 0.005mm, as rolled, 99.9%

Nickel, rod, 200mm, diameter 10.0mm, 99.99+%

Nickel, foil, light tested, 100x100mm, thickness 0.05mm, 99.9%

Nickel, foil, 0.5m coil, thickness 0.0125mm, 99.9%

Nickel, foil, not light tested, 300x300mm, thickness 0.0125mm, 99.9%

Nickel, foil, not light tested, 25x25mm, thickness 0.001mm, 99.95%

Nickel, foil, 1m coil, thickness 0.075mm, annealed, 99%

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

Nickel, foil, light tested, 25x25mm, thickness 0.025mm, annealed, 99%

Nickel, foil, 100x100mm, thickness 0.25mm, as rolled, 99.99+%

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, rod, 1000mm, diameter 3.0mm, 99%

Nickel, foil, 10mm disks, thickness 0.05mm, 99.9%

Nickel, foil, light tested, 300x300mm, thickness 0.02mm, 99.9%

Nickel, tube, 500mm, outside diameter 0.65mm, inside diameter 0.384mm, wall thickness 0.133mm, as drawn, 99.5%

Nickel, foil, 25mm disks, thickness 0.038mm, 99.9%