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

373206

Sigma-Aldrich

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

267112

Sigma-Aldrich

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267082

Sigma-Aldrich

Palladium, sponge, 99.9% trace metals basis

267120

Sigma-Aldrich

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203939

Sigma-Aldrich

Palladium, powder, 99.995% trace metals basis

464651

Sigma-Aldrich

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

686468

Sigma-Aldrich

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

GF60084424

Palladium, foil, light tested, 100x100mm, thickness 0.025mm, as rolled, 99.99+%

GF44874995

Palladium, foil, light tested, 100x100mm, thickness 0.047mm, as rolled, 99.95%

GF57528816

Palladium, foil, not light tested, 25x25mm, thickness 0.006mm, 99.95%

GF55924241

Palladium, foil, not light tested, 25x25mm, thickness 0.025mm, as rolled, 99.99+%

GF81839447

Palladium, foil, light tested, 25x25mm, thickness 0.004mm, 99.95%

GF55245821

Palladium, foil, not light tested, 100x100mm, thickness 0.025mm, as rolled, 99.99+%

GF69074916

Palladium, foil, not light tested, 25x25mm, thickness 0.00075mm, permanent polyester support, 99.75%

GF17495084

Palladium, foil, 10mm disks, thickness 0.03mm, as rolled, 99.95%

GF48798376

Palladium, foil, 25x25mm, thickness 0.1mm, as rolled, 99.99+%

GF34781418

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

GF38720471

Palladium, foil, 4mm disks, thickness 0.025mm, as rolled, 99.95%

GF25018422

Palladium, foil, 6mm disks, thickness 0.075mm, as rolled, 99.95%

GF32271656

Palladium, foil, 4mm disks, thickness 0.02mm, as rolled, 99.95%

GF06612847

Palladium, foil, 0.1m coil, thickness 0.1mm, coil width 2mm, as rolled, 99.95%

GF12749463

Palladium, foil, 10mm disks, thickness 0.047mm, as rolled, 99.95%

GF25547351

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

GF33956949

Palladium, foil, 6mm disks, thickness 0.02mm, as rolled, 99.95%

GF21832747

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

GF65258703

Palladium, foil, 4mm disks, thickness 0.03mm, as rolled, 99.95%

GF00367422

Palladium, foil, 15mm disks, thickness 0.025mm, as rolled, 99.99+%

GF98544527

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