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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

摘要

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.

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铜, powder, 99.999% trace metals basis

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

Sigma-Aldrich

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

Sigma-Aldrich

铜, wire, diam. 1.0 mm, ≥99.9%

Sigma-Aldrich

铜, powder (spheroidal), 10-25 μm, 98%

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

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

Sigma-Aldrich

铜, powder, <75 μm, 99%

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

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

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铜, foil, ≥99.8% (complexometric)

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

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铜, turnings, purum p.a., ≥99.0%

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

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

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

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铜, shot, −3-+14 mesh, 99%

Sigma-Aldrich

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

铜, rod, 50mm, diameter 6.35mm, as drawn, 99.999%

Sigma-Aldrich

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

铜, mesh, 100x100mm, nominal aperture 0.14mm, thickness 0.25mm, wire diameter 0.115mm, 100x100 wires/inch, open area 30.3%, plain weave mesh

铜, tube, 100mm, outside diameter 3.5mm, inside diameter 1.56mm, wall thickness 0.97mm, as drawn, 99.9%

铜, foil, 100x100mm, thickness 0.1mm, hard, 99.95+%

Sigma-Aldrich

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

Sigma-Aldrich

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

铜, insulated wire, 50m, conductor diameter 0.05mm, insulation thickness 0.002mm, 2 micron polyesterimide insulation, 99.9%

铜, sheet, 150x150mm, thickness 3.0mm, 99.95+%

铜, rod, 1000mm, diameter 4.8mm, hard, 99.9%

铜, wire reel, 50m, diameter 0.5mm, annealed, 99.9%

铜, foil, 25mm disks, thickness 0.25mm, annealed, 99.95+%