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

686468

Sigma-Aldrich

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203939

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373206

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348694

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348643

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267120

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267112

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326666

Sigma-Aldrich

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287474

Sigma-Aldrich

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GF90427866

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

GF23374661

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GF03781863

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

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