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Impact of copper-catalyzed cross-coupling reactions in natural product synthesis: the emergence of new retrosynthetic paradigms.

Impact of copper-catalyzed cross-coupling reactions in natural product synthesis: the emergence of new retrosynthetic paradigms.

Natural product reports (2013-10-25)

Gwilherm Evano, Cédric Theunissen, Alexandre Pradal

ABSTRACT

Copper-catalyzed Ullmann-Goldberg-type cross-coupling reactions have undergone nothing short of a renaissance over the last decade and an impressive number of procedures are now available for the formation of C-N, C-O and C-S bonds with remarkable efficiencies and surgical precision. These reactions have been recently integrated into natural product synthesis, which clearly resulted in the emergence of new retrosynthetic paradigms and bond disconnections. The impact of copper-catalyzed cross-coupling reactions in natural product synthesis will be overviewed in this article with an emphasis on the evolution of strategies due to copper catalysis, mostly by comparison with alternative tactics and their relative efficiencies.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

Sigma-Aldrich

Copper, foil, thickness 1.0 mm, 99.999% trace metals basis

Sigma-Aldrich

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

Sigma-Aldrich

Copper, powder, <75 μm, 99%

Sigma-Aldrich

Copper, beads, 2-8 mm, 99.9995% trace metals basis

Sigma-Aldrich

Copper, foil, thickness 0.5 mm, 99.98% trace metals basis

Sigma-Aldrich

Copper, foil, thickness 0.025 mm, 99.98% trace metals basis

Sigma-Aldrich

Copper, wire, diam. 2.0 mm, 99.999% trace metals basis

Sigma-Aldrich

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

Sigma-Aldrich

Copper, wire, diam. 0.64 mm, 99.995% trace metals basis

Sigma-Aldrich

Copper, wire, diam. 1.0 mm, ≥99.9%

Sigma-Aldrich

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

Sigma-Aldrich

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

Sigma-Aldrich

Copper, powder, 99.999% trace metals basis

Sigma-Aldrich

Copper, shot, −3-+14 mesh, 99%

Sigma-Aldrich

Copper, powder, <425 μm, 99.5% trace metals basis

Sigma-Aldrich

Copper, powder (dendritic), <45 μm, 99.7% trace metals basis

Sigma-Aldrich

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

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

Sigma-Aldrich

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

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

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

Sigma-Aldrich

Copper, nanopowder, 40-60 nm particle size (SAXS), ≥99.5% trace metals basis