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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, powder, <1 μm, ≥99.9% trace metals basis
Sigma-Aldrich
Palladium, powder, 99.995% trace metals basis
Sigma-Aldrich
Palladium black, surface area 40-60 m2/g, 99.95% trace metals basis
Sigma-Aldrich
Palladium, granular, 99.99% trace metals basis
Sigma-Aldrich
Palladium, wire, diam. 0.5 mm, 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, sponge, 99.9% trace metals basis
Sigma-Aldrich
Palladium, foil, thickness 0.5 mm, 99.9% trace metals basis
Sigma-Aldrich
Palladium, foil, thickness 0.05 mm, 99.9% trace metals basis
Palladium, foil, 50x50mm, thickness 0.1mm, as rolled, 99.95%
Palladium, foil, 50x50mm, thickness 0.25mm, as rolled, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.006mm, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.025mm, as rolled, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.025mm, as rolled, 99.99+%
Palladium, foil, light tested, 25x25mm, thickness 0.03mm, as rolled, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.047mm, as rolled, 99.95%
Palladium, foil, light tested, 25x25mm, thickness 0.075mm, as rolled, 99.95%
Palladium, foil, light tested, 50x50mm, thickness 0.025mm, as rolled, 99.99+%
Palladium, foil, light tested, 50x50mm, thickness 0.03mm, as rolled, 99.95%
Palladium, foil, light tested, 50x50mm, thickness 0.047mm, as rolled, 99.95%
Palladium, foil, light tested, 50x50mm, thickness 0.075mm, as rolled, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.004mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.005mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.006mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.008mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.0125mm, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.025mm, as rolled, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.02mm, as rolled, 99.95%
Palladium, foil, not light tested, 100x100mm, thickness 0.03mm, as rolled, 99.95%