Manganese porphyrins as efficient catalysts in solvent-free cyclohexane oxidation
Novel non-symmetric third-generation manganese metalloporphyrins, chlorido(5-(4-nitrophenyl)-10,15,20-triphenyl-2,3,7,8,12,13,17,18 octobromoporphyrinate)manganese(III) (MnBr8P1) and the mixture of isomers chlorido(5,10-(4-nitrophenyl)-15,20-diphenyl-2,3,7,8,12,13,17,18-octabromoporphyrinate)mangane...
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| Format: | Article |
| Language: | English |
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Elsevier
2020-01-01
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| Series: | Arabian Journal of Chemistry |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535217302423 |
| _version_ | 1818912107431723008 |
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| author | Mariana Goes de Araujo Tôrres Vinicius Santos da Silva Ynara Marina Idemori Gilson DeFreitas-Silva |
| author_facet | Mariana Goes de Araujo Tôrres Vinicius Santos da Silva Ynara Marina Idemori Gilson DeFreitas-Silva |
| author_sort | Mariana Goes de Araujo Tôrres |
| collection | DOAJ |
| description | Novel non-symmetric third-generation manganese metalloporphyrins, chlorido(5-(4-nitrophenyl)-10,15,20-triphenyl-2,3,7,8,12,13,17,18 octobromoporphyrinate)manganese(III) (MnBr8P1) and the mixture of isomers chlorido(5,10-(4-nitrophenyl)-15,20-diphenyl-2,3,7,8,12,13,17,18-octabromoporphyrinate)manganese(III) and chlorido(5,15-(4-nitrophenyl)-10,20-diphenyl-2,3,7,8,12,13,17,18-octabromoporphyrinate)manganese(III) (cis/trans-MnBr8P2) were obtained from their second-generation analogues (MnP1 and cis/trans-MnP2). These four catalysts were used in cyclohexane oxidation reactions with iodosylbenzene (PhIO) or iodobenzene diacetate (PhI(OAc)2) in the presence or absence of solvent (CH2Cl2). Cyclohexanol (Cy-ol) and cyclohexanone (Cy-one) were the sole reaction products. Regardless of the system, third-generation catalysts MnBr8P1 and cis/trans-MnBr8P2 performed better than second-generation catalysts (MnP1 and cis/trans-MnP2, respectively). In solvent systems, cis/trans-MnBr8P2 afforded a greater total yield (%Cy-ol + %Cy-one) than systems using MnBr8P1, with an increase from 80 to 89% in PhIO and from 47 to 57% in PhI(OAc)2. The systems without solvent, showed to be viable and presented significant yields with PhIO as oxidant, with total yield of 30% for MnBr8P1, and 55% for cis/trans-MnBr8P2. Additionally, in systems with third-generation catalysts without solvent, selectivity was close to 100% for Cy-ol. Keywords: Manganese porphyrins, Cyclohexane oxidation, Solvent-free reactions, Iodosylbenzene, Iodobenzene diacetate |
| first_indexed | 2024-12-19T23:09:20Z |
| format | Article |
| id | doaj.art-72dfeb2cc15d448a8f3639cc64fd86be |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-19T23:09:20Z |
| publishDate | 2020-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-72dfeb2cc15d448a8f3639cc64fd86be2022-12-21T20:02:16ZengElsevierArabian Journal of Chemistry1878-53522020-01-0113115631574Manganese porphyrins as efficient catalysts in solvent-free cyclohexane oxidationMariana Goes de Araujo Tôrres0Vinicius Santos da Silva1Ynara Marina Idemori2Gilson DeFreitas-Silva3Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, 31.270-901 Belo Horizonte, MG, BrazilCentro de Formação de Professores, Universidade Federal do Recôncavo da Bahia, 45.300-000 Amargosa, BA, BrazilDepartamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, 31.270-901 Belo Horizonte, MG, BrazilDepartamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, 31.270-901 Belo Horizonte, MG, Brazil; Corresponding author.Novel non-symmetric third-generation manganese metalloporphyrins, chlorido(5-(4-nitrophenyl)-10,15,20-triphenyl-2,3,7,8,12,13,17,18 octobromoporphyrinate)manganese(III) (MnBr8P1) and the mixture of isomers chlorido(5,10-(4-nitrophenyl)-15,20-diphenyl-2,3,7,8,12,13,17,18-octabromoporphyrinate)manganese(III) and chlorido(5,15-(4-nitrophenyl)-10,20-diphenyl-2,3,7,8,12,13,17,18-octabromoporphyrinate)manganese(III) (cis/trans-MnBr8P2) were obtained from their second-generation analogues (MnP1 and cis/trans-MnP2). These four catalysts were used in cyclohexane oxidation reactions with iodosylbenzene (PhIO) or iodobenzene diacetate (PhI(OAc)2) in the presence or absence of solvent (CH2Cl2). Cyclohexanol (Cy-ol) and cyclohexanone (Cy-one) were the sole reaction products. Regardless of the system, third-generation catalysts MnBr8P1 and cis/trans-MnBr8P2 performed better than second-generation catalysts (MnP1 and cis/trans-MnP2, respectively). In solvent systems, cis/trans-MnBr8P2 afforded a greater total yield (%Cy-ol + %Cy-one) than systems using MnBr8P1, with an increase from 80 to 89% in PhIO and from 47 to 57% in PhI(OAc)2. The systems without solvent, showed to be viable and presented significant yields with PhIO as oxidant, with total yield of 30% for MnBr8P1, and 55% for cis/trans-MnBr8P2. Additionally, in systems with third-generation catalysts without solvent, selectivity was close to 100% for Cy-ol. Keywords: Manganese porphyrins, Cyclohexane oxidation, Solvent-free reactions, Iodosylbenzene, Iodobenzene diacetatehttp://www.sciencedirect.com/science/article/pii/S1878535217302423 |
| spellingShingle | Mariana Goes de Araujo Tôrres Vinicius Santos da Silva Ynara Marina Idemori Gilson DeFreitas-Silva Manganese porphyrins as efficient catalysts in solvent-free cyclohexane oxidation Arabian Journal of Chemistry |
| title | Manganese porphyrins as efficient catalysts in solvent-free cyclohexane oxidation |
| title_full | Manganese porphyrins as efficient catalysts in solvent-free cyclohexane oxidation |
| title_fullStr | Manganese porphyrins as efficient catalysts in solvent-free cyclohexane oxidation |
| title_full_unstemmed | Manganese porphyrins as efficient catalysts in solvent-free cyclohexane oxidation |
| title_short | Manganese porphyrins as efficient catalysts in solvent-free cyclohexane oxidation |
| title_sort | manganese porphyrins as efficient catalysts in solvent free cyclohexane oxidation |
| url | http://www.sciencedirect.com/science/article/pii/S1878535217302423 |
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