Cytochrome P-450 model reactions: efficient and highly selective oxidation of alcohols with tetrabutylammonium peroxymonosulfate catalyzed by Mn-porphyrins.
A novel biomimetic method for rapid oxidation of a wide range of benzylic, allylic, aliphatic, primary and secondary alcohols to the related aldehydes and ketones using Bu(4)NHSO(5) catalyzed by Mn(TPP)OAc/pyridine system with high to excellent yields and excellent selectivity has been developed. The high turnover rates obtained in this catalytic system represent a high efficiency and also relative stability of Mn-porphyrin catalyst towards oxidative degradation. The presence of an electron-withdrawing group on the phenyl ring of both benzyl alcohol and porphyrin ligand increases the reactivity of substrate as well as catalytic activity of Mn-porphyrin catalyst in the oxidation reaction.
Rezaeifard
Abdolreza
A
Department of Chemistry, Faculty of Science, University of Birjand, 414 Birjand, Iran. rrezaeifard@birjand.ac.ir
Jafarpour
Maasoumeh
M
Moghaddam
Gholamreza Kardan
GK
Amini
Fatemeh
F
D000438:Alcohols / Q000737:chemistry*; D000447:Aldehydes / Q000138:chemical synthesis; D002384:Catalysis; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry*; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry; D007700:Kinetics; D008345:Manganese; D010084:Oxidation-Reduction; D011166:Porphyrins / Q000138:chemical synthesis* / Q000494:pharmacology*; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012997:Solvents
D000438:Alcohols; D000447:Aldehydes; D007202:Indicators and Reagents; D007659:Ketones; D011166:Porphyrins; D000644:Quaternary Ammonium Compounds; D012997:Solvents; D008345:Manganese; D003577:Cytochrome P-450 Enzyme System; C009405:tetrabutylammonium