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

摘要

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.

材料

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577995

Sigma-Aldrich

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

510033

Sigma-Aldrich

Raney^®-镍, W.R. Grace and Co. Raney^® 2400, slurry, in H₂O, active catalyst

203904

Sigma-Aldrich

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

GF21346848

镍, rod, 100mm, diameter 1.5mm, 99.99+%

357553

Sigma-Aldrich

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

357634

Sigma-Aldrich

镍, wire, diam. 0.25 mm, ≥99.9%

267074

Sigma-Aldrich

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

GF56791378

镍, pellets, 100g, max. size 10mm, 99.999%

357626

Sigma-Aldrich

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

GF37939506

镍, mesh, 30x30mm, nominal aperture 0.34mm, thickness 0.025mm, wire diameter 0.041mm, 70 wires/inch, open area 80%, electro-formed mesh, 99.9%

267058

Sigma-Aldrich

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

357588

Sigma-Aldrich

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

767484

Sigma-Aldrich

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

267007

Sigma-Aldrich

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

GF86063654

镍, foil, 100x100mm, thickness 1.6mm, 99%

GF72121159

镍, foil, light tested, 150x150mm, thickness 0.025mm, 99.9%

GF04391591

镍, mesh, 100x250mm, nominal aperture 0.73mm, wire diameter 0.25mm, 26x26 wires/inch, open area 55%, plain weave mesh, 99%

GF17897596

镍, pellets, 100g, max. size 5mm, 99.99+%

GF89678570

镍, wire reel, 100m, diameter 0.025mm, as drawn, 99.98%

GF55371832

镍, mesh, 65x65mm, nominal aperture 0.34mm, thickness 0.025mm, wire diameter 0.041mm, 70 wires/inch, open area 80%, electro-formed mesh, 99.9%

GF60569455

镍, foil, 100x100mm, thickness 0.1mm, annealed, 99%

GF90261547

镍, mesh, 130x130mm, nominal aperture 0.04mm, thickness 0.004mm, wire diameter 0.011mm, 500 wires/inch, open area 60%, electro-formed mesh, 99.9%

GF18587975

镍, sphere, 100pcs, diameter 1.0mm, precision sphere grade 200, 99%

GF97780315

镍, foil, 200x200mm, thickness 0.1mm, annealed, 99%

GF56481969

镍, pellets, 20g, max. size 5mm, 99.99+%

GF71556958

镍, rod, 200mm, diameter 2.0mm, annealed, 99%

GF07235131

镍, mesh, 240x240mm, nominal aperture 0.43mm, thickness 0.004mm, wire diameter 0.067mm, 51 wires/inch, open area 75%, electro-formed mesh, 99.9%

GF27854196

镍, foil, 50x50mm, thickness 1.6mm, 99%

GF35122092

镍, mesh, 65x65mm, nominal aperture 0.04mm, thickness 0.004mm, wire diameter 0.011mm, 500 wires/inch, open area 60%, electro-formed mesh, 99.9%

GF10085240

镍, pellets, 20g, max. size 10mm, 99.99+%