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

BCR058

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

61139

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

12816

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

266744

Sigma-Aldrich

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

254177

Sigma-Aldrich

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

326488

Sigma-Aldrich

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

207780

Sigma-Aldrich

Copper, powder, <75 μm, 99%

GF06880507

Copper - O.F.H.C., foil, 6mm disks, thickness 0.1mm, hard, 99.95+%

GF15555876

Copper - O.F.H.C., foil, not light tested, 200x200mm, thickness 0.006mm, hard, 99.95+%

GF56398001

Copper - O.F.H.C., tube, 200mm, outside diameter 9.5mm, inside diameter 7.9mm, wall thickness 0.8mm, 99.95+%

GF48272890

Copper - O.F.H.C., tube, 100mm, outside diameter 2.54mm, inside diameter 1.54mm, wall thickness 0.5mm, 99.95+%

GF86047959

Copper - O.F.H.C., wire reel, 100m, diameter 0.80mm, as drawn, 99.95+%

GF33500607

Copper - O.F.H.C., rod, 200mm, diameter 50.0mm, as drawn, 99.95+%

GF96885905

Copper - O.F.H.C., rod, 100mm, diameter 16mm, as drawn, 99.95+%

GF27357240

Copper - O.F.H.C., foil, light tested, 25x25mm, thickness 0.075mm, half hard, 99.95+%

GF58595675

Copper - O.F.H.C., tube, 200mm, outside diameter 1.23mm, inside diameter 0.51mm, wall thickness 0.36mm, 99.95+%

GF87182657

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

GF16694006

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

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%

GF77355579

Copper, tube, 1000mm, outside diameter 0.65mm, inside diameter 0.21mm, wall thickness 0.22mm, as drawn, 99.9%

GF60058346

Copper, sphere, 1000pcs, diameter 3.0mm, precision sphere grade 200

GF23864463

Copper, tube, 1000mm, outside diameter 0.75mm, inside diameter 0.23mm, wall thickness 0.26mm, as drawn, 99.9%

349216

Sigma-Aldrich

Copper, wire, diam. 1.0 mm, ≥99.9%

349151

Sigma-Aldrich

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

326429

Sigma-Aldrich

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

349224

Sigma-Aldrich

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

326410

Sigma-Aldrich

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

349208

Sigma-Aldrich

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

GF39045090

Copper, wire reel, 100m, diameter 0.075mm, annealed, 99.9%