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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, beads, 2-8 mm, ≥99.99% trace metals basis
Sigma-Aldrich
Copper, turnings, purum p.a., ≥99.0%
Continuous cast copper (O), BCR®, certified reference material, rod
Sigma-Aldrich
Copper, foil, ≥99.8% (complexometric)
Sigma-Aldrich
Copper, beads, 2-8 mm, 99.9995% trace metals basis
Sigma-Aldrich
Copper, foil, thickness 1.0 mm, 99.999% 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, powder, <75 μm, 99%
Copper - O.F.H.C., foil, 6mm disks, thickness 1.0mm, half hard, 99.95+%
Copper - O.F.H.C., foil, 8mm disks, thickness 0.25mm, half hard, 99.95+%
Copper - O.F.H.C., foil, light tested, 150x150mm, thickness 0.05mm, annealed, 99.95+%
Copper - O.F.H.C., foil, light tested, 150x150mm, thickness 0.05mm, hard, 99.95+%
Copper - O.F.H.C., foil, light tested, 25x25mm, thickness 0.006mm, hard, 99.95+%
Copper - O.F.H.C., foil, light tested, 25x25mm, thickness 0.010mm, hard, 99.95+%
Copper - O.F.H.C., foil, 8mm disks, thickness 0.006mm, hard, 99.95+%
Copper - O.F.H.C., foil, 300x300mm, thickness 0.1mm, hard, 99.95+%
Copper - O.F.H.C., foil, 50x50mm, thickness 2.0mm, half hard, 99.95+%
Copper - O.F.H.C., foil, 300x300mm, thickness 0.20mm, hard, 99.95+%
Copper - O.F.H.C., foil, 0.5m coil, thickness 0.125mm, hard, 99.95+%
Copper - O.F.H.C., foil, 100x100mm, thickness 2.0mm, half hard, 99.95+%
Copper - O.F.H.C., foil, 0.5m coil, thickness 0.006mm, hard, 99.95+%
Copper - O.F.H.C., foil, 50x50mm, thickness 0.1mm, hard, 99.95+%
Copper - O.F.H.C., foil, 150x150mm, thickness 0.125mm, hard, 99.95+%
Copper - O.F.H.C., foil, 100x100mm, thickness 0.1mm, half hard, 99.95+%
Copper, mesh, 100x100mm, nominal aperture 0.38mm, wire diameter 0.25mm, 40x40 wires/inch, open area 37%, plain weave mesh
Copper - O.F.H.C., foil, 100x100mm, thickness 0.7mm, half hard, 99.95+%
Copper - O.F.H.C., foil, 300x300mm, thickness 0.1mm, half hard, 99.95+%
Copper, mesh, 65x65mm, nominal aperture 0.2mm, thickness 0.004mm, wire diameter 0.0125mm, 118 wires/inch, open area 88%, electro-formed mesh
Copper, mesh, 150x150mm, nominal aperture 0.14mm, thickness 0.25mm, wire diameter 0.115mm, 100x100 wires/inch, open area 30.3%, plain weave mesh