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Iodocyclization, followed by palladium-catalyzed coupling: a versatile strategy for heterocyclic library construction.

Iodocyclization, followed by palladium-catalyzed coupling: a versatile strategy for heterocyclic library construction.

Combinatorial chemistry & high throughput screening (2012-01-26)

Anton V Dubrovskiy, Nataliya A Markina, Richard C Larock

ABSTRACT

The iodocyclization of functionally-substituted alkynes provides an excellent way to prepare a wide range of iodoheterocycles, which can then be readily elaborated through palladium-catalyzed Suzuki-Miyaura, Sonogashira, Heck, Hartwig-Buchwald, and carbonylation processes into libraries of medicinally relevant heterocycles. The synthesis of libraries of indoles, benzofurans, benzothiophenes, isocoumarins and pyrones, cyclic imidates, isoxazoles, furans using this approach is reviewed. This technology is very versatile, proceeds under mild reaction conditions in high yields, and tolerates considerable functionality.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Palladium, powder, 99.995% trace metals basis

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Palladium, sponge, 99.9% trace metals basis

Palladium, foil, 8mm disks, thickness 0.025mm, as rolled, 99.99+%

Palladium, foil, 8mm disks, thickness 0.03mm, as rolled, 99.95%

Palladium, foil, 4mm disks, thickness 0.006mm, 99.95%

Palladium, foil, 50x50mm, thickness 0.125mm, as rolled, 99.95%

Palladium, foil, 15mm disks, thickness 0.008mm, 99.95%

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

Palladium, foil, 4mm disks, thickness 0.25mm, as rolled, 99.95%

Palladium, foil, 15mm disks, thickness 0.075mm, as rolled, 99.95%

Palladium, foil, 10mm disks, thickness 0.0125mm, 99.95%

Palladium, foil, 10x10mm, thickness 0.50mm, as rolled, 99.95%

Palladium, foil, 25x25mm, thickness 0.25mm, as rolled, 99.95%

Palladium, foil, 4mm disks, thickness 0.008mm, 99.95%

Palladium, foil, 10mm disks, thickness 0.50mm, as rolled, 99.95%

Palladium, foil, 50x50mm, thickness 0.1mm, as rolled, 99.95%

Palladium, foil, 8mm disks, thickness 0.008mm, 99.95%

Palladium, foil, 15mm disks, thickness 0.125mm, as rolled, 99.95%

Palladium, foil, 10mm disks, thickness 0.025mm, as rolled, 99.95%

Palladium, foil, 4mm disks, thickness 0.0125mm, 99.95%