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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, 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

Sigma-Aldrich

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

Nickel, foil, 10mm disks, thickness 0.1mm, annealed, 99%

Nickel, foil, 10mm disks, thickness 0.20mm, annealed, 99%

Nickel, foil, 10mm disks, thickness 0.5mm, as rolled, 100%

Nickel, rod, 200mm, diameter 30mm, 99%

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

Nickel, rod, 500mm, diameter 20.0mm, 99%

Nickel, rod, 200mm, diameter 40mm, 99%

Nickel, rod, 100mm, diameter 3.3mm, 99.99+%

Nickel, rod, 100mm, diameter 20.0mm, 99%

Nickel, rod, 200mm, diameter 12.7mm, 99.98%

Nickel, rod, 200mm, diameter 1.5mm, 99.99+%

Nickel, foil, 10mm disks, thickness 0.05mm, as rolled, 100%

Nickel, rod, 200mm, diameter 6.35mm, 99%

Nickel, foil, 10mm disks, thickness 0.25mm, as rolled, 99.99+%

Nickel, tube, 1000mm, outside diameter 1.8mm, inside diameter 1.6mm, wall thickness 0.1mm, hard, 99.5%

Nickel, foil, 4mm disks, thickness 0.125mm, as rolled, 100%

Nickel, foil, 50mm disks, thickness 0.03mm, 99.9%

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

Nickel, foil, 50mm disks, thickness 0.15mm, annealed, 99%

Nickel, foil, 50mm disks, thickness 0.0125mm, 99.99+%

Nickel, foil, 50mm disks, thickness 0.025mm, annealed, 99%

Nickel, foil, 50mm disks, thickness 0.075mm, as rolled, 99.98%

Nickel, foil, 5m coil, thickness 0.05mm, coil width 2mm, annealed, 99%

Nickel, foil, light tested, 300x300mm, thickness 0.05mm, annealed, 99%

Nickel, foil, not light tested, 300x300mm, thickness 0.0125mm, annealed, 99%