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Solvent dependent reductive defluorination of aliphatic C-F bonds employing Sm(HMDS)2.

Solvent dependent reductive defluorination of aliphatic C-F bonds employing Sm(HMDS)2.

Chemical communications (Cambridge, England) (2013-01-30)

Mario Janjetovic, Annika M Träff, Tobias Ankner, Jenny Wettergren, Göran Hilmersson

ABSTRACT

Sm(HMDS)(2) in n-hexane mediates fast cleavage of primary, secondary and tertiary alkyl fluorides in good to excellent yields. In n-hexane Sm(HMDS)(2) exhibits uniquely enhanced reductive ability towards the C-F bond compared to when using THF as solvent.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Tris[N,N-bis(trimethylsilyl)amide]yttrium

Sigma-Aldrich

Tris[N,N-bis(trimethylsilyl)amide]samarium(III), 98%

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide, 97%

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 1 M in tert-butyl methyl ether

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 1 M in toluene

Sigma-Aldrich

Potassium bis(trimethylsilyl)amide solution, 1 M in THF

Sigma-Aldrich

Potassium bis(trimethylsilyl)amide, 95%

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 1.0 M in THF

Sigma-Aldrich

Samarium, −40 mesh, 99% trace rare earth metals basis

Sigma-Aldrich

Potassium bis(trimethylsilyl)amide solution, 0.5 M in toluene

Sigma-Aldrich

Sodium bis(trimethylsilyl)amide solution, 1.0 M in THF

Sigma-Aldrich

Hexamethyldisilazane, produced by Wacker Chemie AG, Burghausen, Germany, ≥97.0% (GC)

Supelco

Hexamethyldisilazane, for GC derivatization, LiChropur^™, ≥99.0% (GC)

Sigma-Aldrich

Sodium bis(trimethylsilyl)amide solution, 40% in THF

Sigma-Aldrich

Sodium bis(trimethylsilyl)amide solution, 0.6 M in toluene

Sigma-Aldrich

Sodium bis(trimethylsilyl)amide, 95%

Sigma-Aldrich

Hexamethyldisilazane, reagent grade, ≥99%

Sigma-Aldrich

Hexamethyldisilazane, ReagentPlus^®, 99.9%

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 1.0 M in hexanes

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 1.5 M in THF

Sigma-Aldrich

Potassium bis(trimethylsilyl)amide solution, 1.0 M in 2-methyltetrahydrofuran

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 0.5 M in 2-methyltetrahydrofuran