Effect of l-cysteine on the oxidation of cyclohexane catalyzed by manganeseporphyrin

• Published in: Bioorganic & medicinal chemistry letters Vol. 25; no. 11; pp. 2356 - 2359
• Main Authors: Zhou, Wei-You, Tian, Peng, Chen, Yong, He, Ming-Yang, Chen, Qun, Chen, Zai Xin
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01.06.2015
• Subjects: Biomimetic catalysis; Catalysis; Cocatalyst; Cyclohexanes - chemistry; Cysteine - chemistry; l-Cysteine; Manganese - chemistry; Manganese tetra-phenylporphyrin; Molecular Structure; Oxidation-Reduction; Porphyrins - chemistry; Selective oxidation; Selective oxidation; l-Cysteine; Manganese tetra-phenylporphyrin; Cocatalyst; Biomimetic catalysis
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2015.04.020

In the oxidation of cyclohexane by MnTPP, l-cysteine could moderately improve the catalytic activity of MnTPP and significantly increase the selectivity of cyclohexanol. The l-cysteine may perform dual roles in the catalytic oxidation. [Display omitted] Effect of l-cysteine as the cocatalyst on the oxidation of cyclohexane by tert-butylhydroperoxide (TBHP) catalyzed by manganese tetraphenylporphyrin (MnTPP) has been investigated. The results showed that l-cysteine could moderately improve the catalytic activity of MnTPP and significantly increase the selectivity of cyclohexanol. Different from imidazole and pyridine, the l-cysteine may perform dual roles in the catalytic oxidation of cyclohexane. Besides as the axial ligand for MnTPP, the l-cysteine could also react with cyclohexyl peroxide formed as the intermediate to produce alcohol as the main product.