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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

Raney^®-Nickel, W.R. Grace and Co. Raney^® 4200, slurry, in H₂O, active catalyst

Sigma-Aldrich

Nickel, foil, thickness 0.125 mm, ≥99.9%

Sigma-Aldrich

Nickel, wire, diam. 0.5 mm, ≥99.99% trace metals basis

Sigma-Aldrich

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

Sigma-Aldrich

Nickel, powder, <1 μm, 99.8% trace metals basis

Sigma-Aldrich

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

Sigma-Aldrich

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

Nickel, foil, 100x100mm, thickness 3.2mm, as rolled, 99.99+%

Sigma-Aldrich

Nickel, sputtering target, diam. × thickness 2.00 in. × 0.25 in., 99.95% trace metals basis

Nickel, broken cathode squares, 500g, max. size 50mm, 99.8%

Sigma-Aldrich

Nickel, wire, diam. 0.25 mm, ≥99.9%

Nickel, wire reel, 50m, diameter 1.0mm, as drawn, 99%

Nickel, rod, 100mm, diameter 2.0mm, annealed, 99%

Nickel, pellets, 100g, max. size 10mm, 99.99+%

Nickel, rod, 100mm, diameter 40mm, 99%

Nickel, rod, 500mm, diameter 12.7mm, 99.98%

Nickel, wire reel, 5m, diameter 0.5mm, as drawn, 99.99+%

Nickel, wire reel, 1m, diameter 2.0mm, hard, 99.98%

Nickel, foil, light tested, 100x100mm, thickness 0.015mm, 99.9%

Nickel, insulated wire, 50m, conductor diameter 0.025mm, insulation thickness 0.0035mm, polyimide insulation

Nickel, wire reel, 200m, diameter 0.125mm, annealed, 99.98%

Nickel, foil, light tested, 25x25mm, thickness 0.015mm, 99.9%

Nickel, foil, 25mm disks, thickness 0.05mm, as rolled, 99.98%

Nickel, rod, 200mm, diameter 3.0mm, 99%

Nickel, tube, 1000mm, outside diameter 2.4mm, inside diameter 2.248mm, wall thickness 0.076mm, hard, 99.5%

Nickel, foil, 50mm disks, thickness 0.003mm, 99.95%

Nickel, foil, 15mm disks, thickness 0.125mm, annealed, 99%

Nickel, foil, 4mm disks, thickness 0.5mm, as rolled, 100%

Nickel, tube, 100mm, outside diameter 1.8mm, inside diameter 1.6mm, wall thickness 0.1mm, hard, 99.5%

Nickel, foil, 1m coil, thickness 0.025mm, coil width 600mm, as rolled, 99%