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Nickel-catalyzed intramolecular [3 + 2 + 2] cycloadditions of alkylidenecyclopropanes. A straightforward entry to fused 6,7,5-tricyclic systems.

Nickel-catalyzed intramolecular [3 + 2 + 2] cycloadditions of alkylidenecyclopropanes. A straightforward entry to fused 6,7,5-tricyclic systems.

Organic letters (2014-09-19)

Lucía Saya, Israel Fernández, Fernando López, José L Mascareñas

ABSTRACT

A highly diastereo- and chemoselective intramolecular nickel-catalyzed cycloaddition of alkene- and alkyne-tethered alkynylidenecyclopropanes is reported. The method constitutes the first fully intramolecular [3 + 2 + 2] alkylidenecyclopropropane cycloaddition occurring via a proximal cleavage of the cyclopropane and makes it possible to build relevant 6,7,5-tricyclic frameworks in a single-pot reaction. Importantly, the reaction outcome is highly dependent on the characteristics of the nickel ligands.

MATERIALS

Product Number

Brand

Product Description

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

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

Nickel, foil, not light tested, 25x25mm, thickness 0.0005mm, temporary acrylic support, 99.95%

Nickel, wire reel, 10m, diameter 0.125mm, annealed, 99.98%

Nickel, wire reel, 0.2m, diameter 0.5mm, as drawn, 99.99+%

Nickel, tube, 500mm, outside diameter 2.8mm, inside diameter 1.8mm, wall thickness 0.5mm, hard, 99.5%

Nickel, foil, 10mm disks, thickness 0.03mm, 99.9%

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

Nickel, tube, 500mm, outside diameter 8.4mm, inside diameter 8.15mm, wall thickness 0.125mm, hard, 99.5%

Nickel, foil, 2m coil, thickness 0.075mm, as rolled, 99.98%

Nickel, foil, 0.5m coil, thickness 0.0125mm, annealed, 99%

Nickel, wire reel, 0.5m, diameter 0.05mm, as drawn, 99.99+%

Nickel, foil, 2m coil, thickness 0.25mm, annealed, 99.98%

Nickel, foil, 0.5m coil, thickness 0.15mm, annealed, 99%

Nickel, wire reel, 100m, diameter 0.5mm, as drawn, 99%

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

Nickel, wire reel, 50m, diameter 0.125mm, hard, 99.98%

Nickel, wire reel, 50m, diameter 0.25mm, hard, 99.98%

Nickel, foil, 25mm disks, thickness 0.125mm, as rolled, 99.99+%

Nickel, tube, 200mm, outside diameter 5.9mm, inside diameter 5.65mm, wall thickness 0.125mm, hard, 99.5%

Nickel, wire reel, 50m, diameter 0.5mm, as drawn, 99%

Nickel, wire reel, 250m, diameter 0.25mm, annealed, 99%

Nickel, wire reel, 500m, diameter 0.125mm, hard, 99.98%

Nickel, foil, 6mm disks, thickness 0.0125mm, 99.9%

Nickel, foil, 6mm disks, thickness 0.038mm, 99.9%

Nickel, wire reel, 500m, diameter 0.15mm, as drawn, 99%