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

207780

Sigma-Aldrich

Copper, powder, <75 μm, 99%

254177

Sigma-Aldrich

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

266744

Sigma-Aldrich

Copper, foil, thickness 1.0 mm, 99.999% 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

349208

Sigma-Aldrich

Copper, foil, thickness 0.025 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

326488

Sigma-Aldrich

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

12816

Sigma-Aldrich

Copper, foil, ≥99.8% (complexometric)

61139

Sigma-Aldrich

Copper, turnings, purum p.a., ≥99.0%

GF37929134

Copper, rod, 500mm, diameter 2.0mm, as drawn, 99.99+%

GF23864463

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

GF20661083

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

GF53474980

Copper, tube, 100mm, outside diameter 12.7mm, inside diameter 10.26mm, wall thickness 1.22mm, as drawn, 99.9%

GF98886920

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

GF87182657

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

GF56894226

Copper - O.F.H.C., foil, light tested, 100x100mm, thickness 0.075mm, half hard, 99.95+%

GF51452300

Copper - O.F.H.C., foil, 6mm disks, thickness 0.7mm, half hard, 99.95+%

GF39253721

Copper - O.F.H.C., sheet, 50x50mm, thickness 4.76mm, 99.95+%

GF35983615

Copper - O.F.H.C., foil, light tested, 150x150mm, thickness 0.05mm, annealed, 99.95+%

GF47647514

Copper - O.F.H.C., foil, light tested, 25x25mm, thickness 0.05mm, annealed, 99.95+%

GF39719627

Copper - O.F.H.C., rod, 100mm, diameter 76mm, as drawn, 99.95+%

GF82273057

Copper, insulated wire, 5m, conductor diameter 0.7mm, insulation thickness 0.01mm, polyurethane insulation

GF14145689

Copper, mesh, 600x600mm, nominal aperture 0.38mm, wire diameter 0.25mm, 40x40 wires/inch, open area 37%, plain weave mesh

GF15689818

Copper, insulated wire, 5m, conductor diameter 0.24mm, insulation thickness 0.25mm, PTFE (polytetrafluoroethylene) insulation

GF99438092

Copper, insulated wire, 5m, conductor diameter 0.45mm, insulation thickness 0.25mm, PTFE (polytetrafluoroethylene) insulation

GF23570962

Copper, insulated wire, 20m, conductor diameter 0.018mm, insulation thickness 0.005mm, polyurethane insulation, 99.99%

GF82482138

Copper, insulated wire, 5m, conductor diameter 1.0mm, insulation thickness 0.25mm, PTFE (polytetrafluoroethylene) insulation