A facile sp3 C–H bonds amidation of N, N-dimethylanilines by a novel ionic iron(III) complex containing an imino-functionalized imidazolium cation. Issue 37 (14th September 2016)

• Record Type: Journal Article
• Authors: Zhu, Fan; Lu, Bing; Sun, Hongmei; Shen, Qi
• Is Part Of: Tetrahedron letters. Volume 57:Issue 37(2016)
• Page Start: 4152
• Page End: 4156
• Publication Date: 2016-09-14
• Subjects: Iron(III) complex -- Imidazolium salts -- Amidation of C–H bond -- N, N-Dimethylanilines; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.07.098
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A novel ionic iron(III) complex has been prepared. Iron-catalyzed the direct sp 3 C–H bond amidation of N, N -dimethylanilines. A new method for synthesis of N -substituted aromatic and aliphatic amides. Abstract: A new imino-functionalized imidazolium salt, 1-[1-(2, 6-diisopropylphenylimino)ethyl]-3-benzylimidazolium chloride ([HL]Cl, ), was designed and used to prepare a novel ionic iron(III) complex [HL][FeCl4 ] (2 ). Complex2 was an efficient and easy-to-use catalyst for the direct sp 3 C–H bond amidation of N, N -dimethylanilines, affording a wide variety of N -substituted aromatic or aliphatic amides in moderate to good yields. This reaction is the first example of iron-catalyzed intermolecular amidation of unactivated sp 3 C–H bonds of tertiary amines by aromatic or aliphatic amides under mild reaction conditions.