Fluorous hydroboration

Fig. 2.7 Fluorous phase catalytic hydroboration. The procedure involves stirring the catalyst (0.1 mol%) in the fluorous phase with neat reactants at 40-45 °C, the cooling on completion of reaction and extracing with THF.

Hydroboration of a variety of alkenes and terminal alkynes with catecholborane in the fluorous solvent perfluoromethylcyclohexane was performed using fluorous analogs of the Wilkinson catalyst.135 136 Recycling of a rhodium-based alkene hydrosilylation catalyst was also successful.137 Activated aromatics and naphthalene showed satisfactory reactivity in Friedel-Crafts acylation with acid anhydrides in the presence of Yb tris(perfluoroalkanesulfonyl)methide catalysts.138... 

Products from hydroboration with catecholborane in fluorous solvents are extractable by THF, while the catalyst [(Cf,Fi3CH2CH2)jP]3RhCl (0.04 mol%) remains in the fluorous... 

This approach has now been applied to a broad range of catalytic reactions, such as hydrogenation, hydroformyla-tion, hydroboration, and many palladium-catalyzed cross-coupling reactions, and excellent catalyst recovery and reuse have been reported. Although there are many comprehensive reviews of fluorous biphase catalysis,the... 

JJJ Juliette, IT Horvath, JA Gladysz. Transition metal catalysis in fluorous media practical application of a new immobilization principle to rhodium-catalyzed hydroboration. Angew Chem hit Ed Engl 36 1610-1612, 1997. 

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