Reduction of hydrazines to amines with aqueous solution of titanium(III) trichloride

Yan Zhang; Qiang Tang; Meiming Luo

doi:10.1039/C1OB05328K

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Organic & Biomolecular Chemistry

Issue 13, 2011

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Reduction of hydrazines to amines with aqueous solution of titanium(III) trichloride

Yan Zhang , Qiang Tang and Meiming Luo

Org. Biomol. Chem., 2011,9, 4977-4982

DOI: 10.1039/C1OB05328K
Received 02 Mar 2011, Accepted 13 Apr 2011
First published on the web 13 Apr 2011

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N–N bond cleavage in hydrazines is widely used in the preparation of amines and thus occupies a significant place in organic synthesis. In this paper, we report a new method for the reductive cleavage of N–N bonds in hydrazines by commercially available and cheap aqueous titanium(III) trichloride. The reaction proceeds smoothly under a broad pH range from acidic to neutral and basic conditions to afford amines in good yields. This method is compatible with substrates containing functionalities such as C–C double bonds, benzyl–nitrogen bonds, benzyloxy and acyl groups.