Solvent-Free Amination of Secondary Benzylic Alcohols with N-Nucleophiles Catalyzed by FeCl₃

Abstract

A general, simple, and environmentally friendly method for the direct amination of secondary benzyl alcohols with amides or 4-nitroaniline is described. This method has been applied to a variety of substrates, and the reaction proceeded smoothly at room temperature under solvent-free conditions. CbzNH₂ was proved to be very useful in the direct preparation of the benzylic amines from corresponding alcohols.

Keywords:

• Amination
• benzyl alcohols
• benzyl amines
• FeCl₃
• solvent free

ACKNOWLEDGMENT

This work was financially supported by the Natural Science Foundation of China (No. 20672035).

Notes

^a Reaction condition: 4-methylbenzenesulfonamide (1.2 mmol), 1-phenylethanol (1 mmol).

^b 4-Methylbenzenesulfonamide was ground before use.

^c Isolated yield.

^a Reaction condition: nucleophile (1.2 mmol), benzylic alcohols (1 mmol), FeCl₃ (20 mol%), room temperature.

^b Isolated yield.

^c When the reactants were both solid, they were ground together and warmed to 60 °C.

^a Isolated yield.