Reduction of halides, sulfonates and epoxides

The reduction of halides or sulfonates is one of the most conventional methods for the synthesis of deoxy sugars. This method is particularly useful for the deoxygenation of primary hydroxyls of carbohydrates. Reduction has been accomplished employing one of the following three methods. 

As mentioned earlier, the introduction of deoxy moieties by reduction has mainly been applied at primary positions. This fact can be attributed 

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Reduction of Halides, Sulfonates, and Epoxides. Aryl to-sylates could be reduced by Ni catalyst and NaBHj under mild conditions. In the presence of a catalytic amount of Ni(PPh3)4Cl2 (7 mol %) and an electron-rich monodentate phosphine ligand such as tricyclohexylphosphine (PCy3) (28 mol %), hydrogenolysis of various aryl tosylates was achieved in high yields (47-100%) (eq 35). 

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