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Copper-catalyzed oxidative decarboxylative couplings of sulfoximines and aryl propiolic acids.

Copper-catalyzed oxidative decarboxylative couplings of sulfoximines and aryl propiolic acids.

Organic letters (2013-11-28)

Daniel L Priebbenow, Peter Becker, Carsten Bolm

ABSTRACT

A method has been developed for the preparation of N-alkynylated sulfoximines involving the copper-catalyzed decarboxylative coupling of sulfoximines with aryl propiolic acids. A range of substituents on both the sulfoximidoyl moiety and the aryl group of the propiolic acid were compatible with this reaction process to afford a series of sulfoximidoyl-functionalized alkynes.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Copper, powder (spheroidal), 10-25 μm, 98%

Sigma-Aldrich

Copper, powder, 99.999% trace metals basis

Sigma-Aldrich

Propiolic acid, 95%

Sigma-Aldrich

Copper, ACS reagent, granular, 10-40 mesh, ≥99.90%

Sigma-Aldrich

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

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Copper, IRMM^®, certified reference material, 0.1 mm foil

Copper, IRMM^®, certified reference material, 0.5 mm wire

Copper (O), BCR^®, certified reference material, rod

Copper (S, P), BCR^®, certified reference material, chips

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Copper, nanopowder, 60-80 nm particle size (SAXS), ≥99.5% trace metals basis

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Copper, beads, 2-8 mm, ≥99.99% trace metals basis

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Copper, turnings, purum p.a., ≥99.0%

Sigma-Aldrich

Copper, wire, diam. 0.25 mm, 99.999% trace metals basis

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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Continuous cast copper (O), BCR^®, certified reference material, rod