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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

Copper (O), BCR®, certified reference material, rod
Sigma-Aldrich
Copper, powder, 99.999% trace metals basis
Sigma-Aldrich
Copper, shot, −3-+14 mesh, 99%
Sigma-Aldrich
Copper, ACS reagent, granular, 10-40 mesh, ≥99.90%
Copper (S, P), BCR®, certified reference material, chips
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
Sigma-Aldrich
Copper, powder (spheroidal), 10-25 μm, 98%
Copper, IRMM®, certified reference material, 0.5 mm wire
Copper, IRMM®, certified reference material, 0.1 mm foil
Sigma-Aldrich
Copper, powder, <425 μm, 99.5% trace metals basis
Copper, tube, 1000mm, outside diameter 6.35mm, inside diameter 4.93mm, wall thickness 0.71mm, as drawn, 99.9%
Copper, tube, 1000mm, outside diameter 2.5mm, inside diameter 1.9mm, wall thickness 0.3mm, as drawn, 99.9%
Copper, tube, 100mm, outside diameter 0.25mm, inside diameter 0.05mm, wall thickness 0.1mm, as drawn, 99.9%
Copper, rod, 50mm, diameter 5.0mm, as drawn, 99.999%
Copper, tube, 1000mm, outside diameter 3.0mm, inside diameter 1.2mm, wall thickness 0.9mm, as drawn, 99.9%
Copper, tube, 100mm, outside diameter 0.95mm, inside diameter 0.29mm, wall thickness 0.33mm, as drawn, 99.9%
Copper, tube, 1000mm, outside diameter 3.5mm, inside diameter 1.56mm, wall thickness 0.97mm, as drawn, 99.9%
Copper, tube, 1000mm, outside diameter 4.0mm, inside diameter 3.2mm, wall thickness 0.4mm, as drawn, 99.9%
Copper, rod, 50mm, diameter 16mm, as drawn, 99.99+%
Copper, sphere, 100pcs, diameter 1.0mm, precision sphere grade 200
Copper, tube, 100mm, outside diameter 1.2mm, inside diameter 0.56mm, wall thickness 0.32mm, as drawn, 99.9%
Copper, tube, 100mm, outside diameter 1.5mm, inside diameter 0.6mm, wall thickness 0.45mm, as drawn, 99.9%
Copper, rod, 500mm, diameter 9.5mm, hard, 99.9%
Copper - O.F.H.C., tube, 200mm, outside diameter 10mm, inside diameter 8mm, wall thickness 1.0mm, 99.95+%
Copper - O.F.H.C., tube, 100mm, outside diameter 8.0mm, inside diameter 6mm, wall thickness 1.0mm, 99.95+%
Copper - O.F.H.C., wire reel, 10m, diameter 0.75mm, as drawn, 99.95+%
Copper - O.F.H.C., wire reel, 50m, diameter 0.80mm, as drawn, 99.95+%
Copper - O.F.H.C., wire reel, 100m, diameter 0.125mm, annealed, 99.95+%
Copper - O.F.H.C., foil, 150x150mm, thickness 0.25mm, half hard, 99.95+%