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

254177

Sigma-Aldrich

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

207780

Sigma-Aldrich

Copper, powder, <75 μm, 99%

349208

Sigma-Aldrich

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

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

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

326429

Sigma-Aldrich

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

326488

Sigma-Aldrich

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

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)

GF23864463

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

GF93436926

Copper, tube, 1000mm, outside diameter 0.95mm, inside diameter 0.29mm, wall thickness 0.33mm, as drawn, 99.9%

GF69447280

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

GF53960283

Copper - O.F.H.C., foil, 150x150mm, thickness 0.25mm, annealed, 99.95+%

GF57685045

Copper - O.F.H.C., wire reel, 20m, diameter 2.5mm, hard, 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+%

GF56545386

Copper - O.F.H.C., foil, 100x100mm, thickness 0.7mm, half hard, 99.95+%

GF46869777

Copper - O.F.H.C., foil, 100x100mm, thickness 0.125mm, hard, 99.95+%

GF48513821

Copper - O.F.H.C., foil, 100x100mm, thickness 0.20mm, hard, 99.95+%

GF95874722

Copper - O.F.H.C., foil, 100x100mm, thickness 1.0mm, half hard, 99.95+%

GF58540675

Copper - O.F.H.C., foil, 25x25mm, thickness 0.1mm, half hard, 99.95+%

GF41864733

Copper, insulated wire, 100m, conductor diameter 0.1mm, insulation thickness 0.015mm, 10-30 micron polyesterimide insulation, 99.9%

GF81367735

Copper - O.F.H.C., wire reel, 5m, diameter 0.125mm, annealed, 99.95+%

GF41581335

Copper - O.F.H.C., foil, 100x100mm, thickness 0.25mm, annealed, 99.95+%

GF92500477

Copper - O.F.H.C., foil, 100x100mm, thickness 2.0mm, half hard, 99.95+%

GF36497773

Copper, insulated wire, 10m, conductor diameter 0.1mm, insulation thickness 0.005mm, polyurethane insulation, 99.9%