Bioinspired manganese complex for room-temperature oxidation of primary amines to imines by t-butyl hydroperoxide

• Published in: Inorganica Chimica Acta 2021-05, Vol.519, p.120282, Article 120282
• Main Authors: Lei, Lin, Chen, Yaju, Feng, Zhenfeng, Deng, Chunyan, Xiao, Yepeng
• Format: Article
• Language: English
• Subjects: Aliphatic amines; Amines; Bioinspired metal complex; Butyl hydroperoxide; Catalysts; Imines; Manganese; Oxidation; Oxidative coupling; Room temperature; Substrates; TBHP
• ISSN: 0020-1693; 1873-3255
• DOI: 10.1016/j.ica.2021.120282

[Display omitted] •The bioinspired MnCl2(TPA)/TBHP catalytic system is simple and sustainable.•MnCl2(TPA) showed high efficiency for room-temperature oxidation of primary amines to imines with TBHP.•MnCl2(TPA) displyed large substrate scope either for aromatic or aliphatic amines. A sustainable method is developed for the selective and additive-free synthesis of imines from primary amines with TBHP catalyzed by bioinspired manganese complex (MnCl2(TPA)) at room temperature. Use of 0.2 mol % MnCl2(TPA) was efficient enough for this transformation by offering excellent conversions up to 98.2% along with 93.4% product yield within 1 h. The influence of reaction parameters (catalyst dosage, solvent, reaction temperature, time, etc.) on the catalytic performance was also investigated in detail. Building on these results, the selected MnCl2(TPA) was further employed to transform various primary amines into corresponding imines and exhibited good compatibility even for the challenging aliphatic amine. The high efficiency, combining with a large substrate scope and ambient reaction conditions, makes the developed bioinspired Mn complex/TBHP system a promising pathway to produce imines. This work also paves a way to the expansion of non-heme metal catalysts as efficient platforms for various oxidation reactions.