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

266744

Sigma-Aldrich

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

207780

Sigma-Aldrich

Copper, powder, <75 μm, 99%

BCR058

Continuous cast copper (O), BCR^®, certified reference material, rod

349151

Sigma-Aldrich

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

349224

Sigma-Aldrich

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

349216

Sigma-Aldrich

Copper, wire, diam. 1.0 mm, ≥99.9%

326429

Sigma-Aldrich

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

349208

Sigma-Aldrich

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

326488

Sigma-Aldrich

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

12816

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

254177

Sigma-Aldrich

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

326410

Sigma-Aldrich

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

61139

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

GF69447280

Copper, tube, 100mm, outside diameter 0.75mm, inside diameter 0.23mm, wall thickness 0.26mm, as drawn, 99.9%

GF94832208

Copper, tube, 1000mm, outside diameter 1.0mm, inside diameter 0.24mm, wall thickness 0.38mm, as drawn, 99.9%

GF16694006

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

GF37804901

Copper, tube, 1000mm, outside diameter 1.2mm, inside diameter 0.56mm, wall thickness 0.32mm, as drawn, 99.9%

GF40548180

Copper, sphere, 200pcs, diameter 3.0mm, precision sphere grade 200

GF98886920

Copper, rod, 50mm, diameter 12.7mm, as drawn, 99.99+%

GF89142701

Copper, tube, 1000mm, outside diameter 5.0mm, inside diameter 4mm, wall thickness 0.5mm, as drawn, 99.9%

GF00529040

Copper, sphere, 100pcs, diameter 3.0mm, precision sphere grade 200

GF87182657

Copper, tube, 1000mm, outside diameter 6.0mm, inside diameter 4mm, wall thickness 1.0mm, as drawn, 99.9%

GF15993423

Copper - O.F.H.C., foil, 0.5m coil, thickness 0.1mm, coil width 100mm, hard, 99.95+%

GF35043702

Copper, insulated wire, 10m, conductor diameter 0.5mm, insulation thickness 0.025mm, polyimide insulation, 99.99%

GF73997386

Copper, microfoil, disks, 10mm, thinness 0.5μm, specific density 448μg/cm², permanent mylar 3.5μm support, 99.99+%

GF84488462

Copper, insulated wire, 5m, conductor diameter 0.5mm, insulation thickness 0.06mm, polyimide insulation

GF53876256

Copper, rod, 200mm, diameter 8.0mm, as drawn, 99.99+%

GF15111458

Copper, rod, 200mm, diameter 9.5mm, hard, 99.9%

GF46821382

Copper, tube, 100mm, outside diameter 1.75mm, inside diameter 0.33mm, wall thickness 0.71mm, as drawn, 99.9%

GF20661083

Copper, tube, 1000mm, outside diameter 12.7mm, inside diameter 10.26mm, wall thickness 1.22mm, as drawn, 99.9%