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  • 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
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Copper, powder (dendritic), <45 μm, 99.7% trace metals basis
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Sigma-Aldrich
Copper, foil, thickness 0.25 mm, 99.98% trace metals basis
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Copper, IRMM®, certified reference material, 0.1 mm foil
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Copper, IRMM®, certified reference material, 0.5 mm wire
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Copper (O), BCR®, certified reference material, rod
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Sigma-Aldrich
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Sigma-Aldrich
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Sigma-Aldrich
Ethyl pentafluoropropionate, 98%
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Sigma-Aldrich
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Copper - O.F.H.C., wire reel, 5m, diameter 0.80mm, as drawn, 99.95+%
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Copper - O.F.H.C., sheet, 150x150mm, thickness 12.7mm, 99.99+%
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Copper - O.F.H.C., foil, light tested, 100x100mm, thickness 0.025mm, hard, 99.95+%
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Copper - O.F.H.C., rod, 200mm, diameter 63.5mm, as drawn, 99.95+%
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Copper - O.F.H.C., rod, 1000mm, diameter 38.1mm, as drawn, 99.95+%
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Copper - O.F.H.C., tube, 100mm, outside diameter 4.0mm, inside diameter 3mm, wall thickness 0.5mm, 99.95+%
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Copper - O.F.H.C., tube, 200mm, outside diameter 4.0mm, inside diameter 3mm, wall thickness 0.5mm, 99.95+%
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Copper - O.F.H.C., sheet, 300x300mm, thickness 4.76mm, 99.95+%
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Copper - O.F.H.C., tube, 200mm, outside diameter 2.54mm, inside diameter 1.54mm, wall thickness 0.5mm, 99.95+%
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Copper - O.F.H.C., rod, 500mm, diameter 25.4mm, as drawn, 99.95+%
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Copper - O.F.H.C., sheet, 150x150mm, thickness 12.7mm, 99.95+%
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Copper - O.F.H.C., tube, 200mm, outside diameter 10mm, inside diameter 8mm, wall thickness 1.0mm, 99.95+%
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Copper - O.F.H.C., tube, 500mm, outside diameter 9.5mm, inside diameter 7.9mm, wall thickness 0.8mm, 99.95+%
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Copper - O.F.H.C., sheet, 300x300mm, thickness 6.35mm, 99.95+%
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Copper - O.F.H.C., tube, 500mm, outside diameter 1.23mm, inside diameter 0.51mm, wall thickness 0.36mm, 99.95+%
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Copper - O.F.H.C., sheet, 50x50mm, thickness 6.35mm, 99.95+%
Pricing and availability is not currently available.