Direct synthesis of pentafluoroethyl copper from pentafluoropropionate as an economical C2F5 source: application to pentafluoroethylation of arylboronic acids and aryl bromides.

Direct synthesis of pentafluoroethyl copper from pentafluoropropionate as an economical C2F5 source: application to pentafluoroethylation of arylboronic acids and aryl bromides.

Organic letters (2014-06-14)

Hiroki Serizawa, Kohsuke Aikawa, Koichi Mikami

KIVONAT

The direct synthesis of pentafluoroethyl copper (CuC2F5) from a cuprate reagent and ethyl pentafluoropropionate as one of the most economical and useful pentafluoroethyl sources was accomplished. The advantages of this method are; all the reagents employed are low-cost and operationally simple, and the CuC2F5 reagent is prepared in virtually quantitative yield. Furthermore, the CuC2F5 reagent prepared was successfully applied to two types of pentafluoroethylations with arylboronic acids and aryl bromides to provide the pentafluoroethylated aromatic products in good-to-excellent yields, including large scale operations.

ANYAGOK

Cikkszám

Márka

Termékleírás

290920

Sigma-Aldrich

Ethyl pentafluoropropionate, 98%

GF66556491

Copper, mesh, 100x100mm, nominal aperture 0.14mm, thickness 0.25mm, wire diameter 0.115mm, 100x100 wires/inch, open area 30.3%, plain weave mesh

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774111

Sigma-Aldrich

Copper, nanopowder, 40-60 nm particle size (SAXS), ≥99.5% trace metals basis

223409

Sigma-Aldrich

Copper, shot, −3-+14 mesh, 99%

IRMM522A

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IRMM522C

Copper, IRMM^®, certified reference material, 0.5 mm wire

311405

Sigma-Aldrich

Copper, ACS reagent, granular, 10-40 mesh, ≥99.90%

BCR054R

Copper (O), BCR^®, certified reference material, rod

774103

Sigma-Aldrich

Copper, nanopowder, 60-80 nm particle size (SAXS), ≥99.5% trace metals basis

203122

Sigma-Aldrich

Copper, powder, 99.99% trace metals basis

266086

Sigma-Aldrich

Copper, powder, <425 μm, 99.5% trace metals basis

349178

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326453

Sigma-Aldrich

Copper, powder (spheroidal), 10-25 μm, 98%

357456

Sigma-Aldrich

Copper, powder (dendritic), <45 μm, 99.7% trace metals basis

BCR017B

Copper (S, P), BCR^®, certified reference material, chips

GF21705140

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

GF81522446

Copper - O.F.H.C., foil, 25x25mm, thickness 0.25mm, half hard, 99.95+%

GF88988562

Copper, insulated wire, 10m, conductor diameter 0.018mm, insulation thickness 0.005mm, polyurethane insulation, 99.99%

GF63314827

Copper - O.F.H.C., wire reel, 5m, diameter 0.80mm, as drawn, 99.95+%

GF90305388

Copper - O.F.H.C., foil, 50x50mm, thickness 0.25mm, half hard, 99.95+%

GF47215133

Copper - O.F.H.C., foil, 150x150mm, thickness 0.5mm, half hard, 99.95+%

GF13707862

Copper - O.F.H.C., foil, 10m coil, thickness 0.05mm, coil width 300mm, half hard, 99.95+%

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Copper, mesh coil, 1m, nominal aperture 0.14mm, thickness 0.25mm, wire diameter 0.115mm, 100x100 wires/inch, open area 30.3%, plain weave mesh

GF24630229

Copper - O.F.H.C., foil, 50x50mm, thickness 0.5mm, half hard, 99.95+%

GF49690996

Copper, insulated wire, 5m, conductor diameter 0.125mm, insulation thickness 0.002mm, 2 micron polyesterimide insulation, 99.9%

GF59685856

Copper - O.F.H.C., foil, 300x500mm, thickness 2.0mm, half hard, 99.95+%

GF17753340

Copper - O.F.H.C., rod, 200mm, diameter 63.5mm, as drawn, 99.95+%

GF96112762

Copper - O.F.H.C., wire reel, 100m, diameter 1.0mm, as drawn, 99.95+%

GF99671619

Copper - O.F.H.C., rod, 50mm, diameter 50.0mm, as drawn, 99.95+%