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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, powder, <425 μm, 99.5% trace metals basis
Sigma-Aldrich
Copper, powder, 99.999% trace metals basis
Sigma-Aldrich
Copper, foil, thickness 0.25 mm, 99.98% trace metals basis
Sigma-Aldrich
Copper, wire, diam. 1.0 mm, ≥99.9%
Sigma-Aldrich
Copper, powder, <75 μm, 99%
Sigma-Aldrich
Copper, powder (spheroidal), 10-25 μm, 98%
Sigma-Aldrich
Copper, ACS reagent, granular, 10-40 mesh, ≥99.90%
Sigma-Aldrich
Copper, nanopowder, 60-80 nm particle size (SAXS), ≥99.5% trace metals basis
Sigma-Aldrich
Copper, nanopowder, 40-60 nm particle size (SAXS), ≥99.5% trace metals basis
Sigma-Aldrich
Copper, electrolytic, Analytical Reagent, reag. Ph. Eur., ≥99.9% (complexometric), wire
Sigma-Aldrich
Copper, foil, thickness 0.025 mm, 99.98% trace metals basis
Sigma-Aldrich
Copper, foil, thickness 1.0 mm, 99.999% trace metals basis
Sigma-Aldrich
Copper, powder (dendritic), <45 μm, 99.7% trace metals basis
Sigma-Aldrich
Copper, foil, thickness 0.5 mm, 99.98% trace metals basis
Sigma-Aldrich
Copper, turnings, purum p.a., ≥99.0%
Sigma-Aldrich
Copper, foil, ≥99.8% (complexometric)
Sigma-Aldrich
Copper, wire, diam. 0.25 mm, 99.999% trace metals basis
Sigma-Aldrich
Copper, beads, 2-8 mm, ≥99.99% trace metals basis
Sigma-Aldrich
Copper, beads, 2-8 mm, 99.9995% trace metals basis
Sigma-Aldrich
Copper, wire, diam. 2.0 mm, 99.999% trace metals basis
Sigma-Aldrich
Copper, wire, diam. 0.64 mm, 99.995% trace metals basis
Copper - O.F.H.C., foil, 150x150mm, thickness 0.20mm, hard, 99.95+%
Copper, wire reel, 100m, diameter 0.05mm, annealed, 99.9%
Copper, wire reel, 1000m, diameter 0.1mm, annealed, 99.9%
Copper, wire reel, 5m, diameter 0.025mm, as drawn, 99.99+%
Copper, wire reel, 1000m, diameter 0.125mm, annealed, 99.9%
Copper - O.F.H.C., foil, 150x150mm, thickness 0.125mm, hard, 99.95+%
Copper, rod, 100mm, diameter 4.8mm, hard, 99.9%
Copper, tube, 100mm, outside diameter 2.0mm, inside diameter 1.6mm, wall thickness 0.2mm, as drawn, 99.9%
Copper, tube, 100mm, outside diameter 2.5mm, inside diameter 1.9mm, wall thickness 0.3mm, as drawn, 99.9%

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