A simple synthesis of anilines by LiAlH4/TiCl4 reduction of aromatic nitro compounds. Issue 39 (23rd September 2015)

• Record Type: Journal Article
• Authors: Di Gioia, Maria Luisa; Leggio, Antonella; Guarino, Isabella Federica; Leotta, Vanessa; Romio, Emanuela; Liguori, Angelo
• Is Part Of: Tetrahedron letters. Volume 56:Issue 39(2015)
• Page Start: 5341
• Page End: 5344
• Publication Date: 2015-09-23
• Subjects: Aromatic nitro compounds -- Lithium aluminum hydride -- Titanium tetrachloride -- Aromatic amines -- Azobenzenes; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.07.089
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A rapid and efficient single-step synthesis of substituted anilines is proposed. Aromatic nitro compounds are reduced to anilines by the reacting system LiAlH4 /TiCl4 . The reducing power of the reactants depends on the molar ratio of LiAlH4 and TiCl4 . The proposed method works well with both 'electron poor' and 'electron rich' substrates. Abstract: A rapid and efficient single-step synthesis of substituted anilines has been developed. The aromatic nitro compounds were reduced by using reducing systems generated by the action of an excess of LiAlH4 on TiCl4 . Anilines substituted with different functional groups were synthesized in high yields and purity starting from the corresponding nitro compounds. The developed procedure is applicable to nitroaromatics containing both electron withdrawing and electron donating substituents. Substrates with electron donor substituents require a larger excess of LiAlH4 . The reducing power of the prepared reactant systems depends on the used molar ratio of LiAlH4 and TiCl4 .