Recent developments and perspectives in palladium-catalyzed cyanation of aryl halides: synthesis of benzonitriles.

Recent developments and perspectives in palladium-catalyzed cyanation of aryl halides: synthesis of benzonitriles.

Chemical Society reviews (2011-04-30)

Pazhamalai Anbarasan, Thomas Schareina, Matthias Beller

ABSTRACT

The palladium-catalyzed cyanation of Ar-X (X = I, Br, Cl, OTf, and H) allows for an efficient access towards benzonitriles. After its discovery in 1973 and following significant improvements in recent decades, this methodology has become nowadays the most popular for preparation of substituted aromatic nitriles. In this critical review, we summarize the important developments in this area from 2000 until 2010 (151 references).

MATERIALS

Product Number

Brand

Product Description

686468

Sigma-Aldrich

Palladium, nanopowder, <25 nm particle size (TEM), ≥99.5%

GF90203475

Palladium, foil, not light tested, 25x25mm, thickness 0.0025mm, 99.95%

GF15900713

Palladium, microfoil, disks, 25mm, thinness 0.5μm, specific density 303.4μg/cm², permanent mylar 3.5μm support, 99.99%

GF81049394

Palladium, foil, not light tested, 50x50mm, thickness 0.0025mm, 99.95%

GF89451489

Palladium, rod, 50mm, diameter 2.0mm, 99.95%

GF21222447

Palladium, foil, not light tested, 50x50mm, thickness 0.02mm, as rolled, 99.95%

GF99402510

Palladium, microfoil, disks, 50mm, thinness 0.05μm, specific density 63.6μg/cm², permanent mylar 3.5μm support, 99.99%

GF01313761

Palladium, foil, not light tested, 50x50mm, thickness 0.002mm, 99.95%

203939

Sigma-Aldrich

Palladium, powder, 99.995% trace metals basis

373206

Sigma-Aldrich

Palladium, evaporation slug, diam. × L 0.6 cm × 0.6 cm, 99.95% trace metals basis

203998

Sigma-Aldrich

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464651

Sigma-Aldrich

Palladium, powder, <75 μm, 99.9% trace metals basis

348694

Sigma-Aldrich

Palladium, wire, diam. 0.5 mm, 99.9% trace metals basis

348678

Sigma-Aldrich

Palladium, foil, thickness 1.0 mm, 99.9% trace metals basis

348643

Sigma-Aldrich

Palladium, foil, thickness 0.25 mm, 99.98% trace metals basis

267082

Sigma-Aldrich

Palladium, sponge, 99.9% trace metals basis

267120

Sigma-Aldrich

Palladium, foil, thickness 0.025 mm, 99.9% trace metals basis

267112

Sigma-Aldrich

Palladium, wire, diam. 1.0 mm, 99.9% trace metals basis

326666

Sigma-Aldrich

Palladium, powder, <1 μm, ≥99.9% trace metals basis

287474

Sigma-Aldrich

Palladium, foil, thickness 0.5 mm, 99.9% trace metals basis

GF90427866

Palladium, foil, light tested, 100x100mm, thickness 0.025mm, as rolled, 99.95%

GF23374661

Palladium, foil, 8mm disks, thickness 0.50mm, as rolled, 99.95%

GF35196330

Palladium, tube, 100mm, outside diameter 2.0mm, inside diameter 1.6mm, wall thickness 0.2mm, as drawn, 99.95%

GF80838704

Palladium, foil, not light tested, 25x25mm, thickness 0.02mm, as rolled, 99.95%

GF43081174

Palladium, foil, not light tested, 100x100mm, thickness 0.0125mm, 99.95%

GF52273852

Palladium, wire reel, 10m, diameter 0.025mm, as drawn, 99.9%

GF03781863

Palladium, foil, light tested, 25x25mm, thickness 0.025mm, as rolled, 99.95%

GF59343688

Palladium, foil, not light tested, 50x50mm, thickness 0.0125mm, 99.95%

GF96367977

Palladium, foil, not light tested, 25x25mm, thickness 0.001mm, permanent polyester support, 99.75%

GF99300371

Palladium, wire reel, 50m, diameter 0.125mm, hard, 99.95%