Recent Synthetic Advances on the Use of Diazo Compounds Catalyzed by Metalloporphyrins
Diazo compounds are organic substances that are often used as precursors in organic synthesis like cyclization reactions, olefinations, cyclopropanations, cyclopropenations, rearrangements, and carbene or metallocarbene insertions into C−H, N−H, O−H, S−H, and Si−H bonds. Typically, reactions from di...
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| Language: | English |
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MDPI AG
2023-09-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/18/6683 |
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| author | Mário M. Q. Simões José A. S. Cavaleiro Vitor F. Ferreira |
| author_facet | Mário M. Q. Simões José A. S. Cavaleiro Vitor F. Ferreira |
| author_sort | Mário M. Q. Simões |
| collection | DOAJ |
| description | Diazo compounds are organic substances that are often used as precursors in organic synthesis like cyclization reactions, olefinations, cyclopropanations, cyclopropenations, rearrangements, and carbene or metallocarbene insertions into C−H, N−H, O−H, S−H, and Si−H bonds. Typically, reactions from diazo compounds are catalyzed by transition metals with various ligands that modulate the capacity and selectivity of the catalyst. These ligands can modify and enhance chemoselectivity in the substrate, regioselectivity and enantioselectivity by reflecting these preferences in the products. Porphyrins have been used as catalysts in several important reactions for organic synthesis and also in several medicinal applications. In the chemistry of diazo compounds, porphyrins are very efficient as catalysts when complexed with low-cost metals (e.g., Fe and Co) and, therefore, in recent years, this has been the subject of significant research. This review will summarize the advances in the studies involving the field of diazo compounds catalyzed by metalloporphyrins (M−Porph, M = Fe, Ru, Os, Co, Rh, Ir) in the last five years to provide a clear overview and possible opportunities for future applications. Also, at the end of this review, the properties of artificial metalloenzymes and hemoproteins as biocatalysts for a broad range of applications, namely those concerning carbene-transfer reactions, will be considered. |
| first_indexed | 2024-03-10T22:24:08Z |
| format | Article |
| id | doaj.art-6cc3ad271f894d968f9f0277c425aa2e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T22:24:08Z |
| publishDate | 2023-09-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj.art-6cc3ad271f894d968f9f0277c425aa2e2023-11-19T12:10:58ZengMDPI AGMolecules1420-30492023-09-012818668310.3390/molecules28186683Recent Synthetic Advances on the Use of Diazo Compounds Catalyzed by MetalloporphyrinsMário M. Q. Simões0José A. S. Cavaleiro1Vitor F. Ferreira2Department of Chemistry & LAQV-REQUIMTE, University of Aveiro, 3810-193 Aveiro, PortugalDepartment of Chemistry & LAQV-REQUIMTE, University of Aveiro, 3810-193 Aveiro, PortugalDepartamento de Tecnologia Farmacêutica Química, Universidade Federal Fluminense, Niterói 24241-002, RJ, BrazilDiazo compounds are organic substances that are often used as precursors in organic synthesis like cyclization reactions, olefinations, cyclopropanations, cyclopropenations, rearrangements, and carbene or metallocarbene insertions into C−H, N−H, O−H, S−H, and Si−H bonds. Typically, reactions from diazo compounds are catalyzed by transition metals with various ligands that modulate the capacity and selectivity of the catalyst. These ligands can modify and enhance chemoselectivity in the substrate, regioselectivity and enantioselectivity by reflecting these preferences in the products. Porphyrins have been used as catalysts in several important reactions for organic synthesis and also in several medicinal applications. In the chemistry of diazo compounds, porphyrins are very efficient as catalysts when complexed with low-cost metals (e.g., Fe and Co) and, therefore, in recent years, this has been the subject of significant research. This review will summarize the advances in the studies involving the field of diazo compounds catalyzed by metalloporphyrins (M−Porph, M = Fe, Ru, Os, Co, Rh, Ir) in the last five years to provide a clear overview and possible opportunities for future applications. Also, at the end of this review, the properties of artificial metalloenzymes and hemoproteins as biocatalysts for a broad range of applications, namely those concerning carbene-transfer reactions, will be considered.https://www.mdpi.com/1420-3049/28/18/6683diazo compoundsporphyrinscarbenesmetallocarbenescatalytic reactions |
| spellingShingle | Mário M. Q. Simões José A. S. Cavaleiro Vitor F. Ferreira Recent Synthetic Advances on the Use of Diazo Compounds Catalyzed by Metalloporphyrins Molecules diazo compounds porphyrins carbenes metallocarbenes catalytic reactions |
| title | Recent Synthetic Advances on the Use of Diazo Compounds Catalyzed by Metalloporphyrins |
| title_full | Recent Synthetic Advances on the Use of Diazo Compounds Catalyzed by Metalloporphyrins |
| title_fullStr | Recent Synthetic Advances on the Use of Diazo Compounds Catalyzed by Metalloporphyrins |
| title_full_unstemmed | Recent Synthetic Advances on the Use of Diazo Compounds Catalyzed by Metalloporphyrins |
| title_short | Recent Synthetic Advances on the Use of Diazo Compounds Catalyzed by Metalloporphyrins |
| title_sort | recent synthetic advances on the use of diazo compounds catalyzed by metalloporphyrins |
| topic | diazo compounds porphyrins carbenes metallocarbenes catalytic reactions |
| url | https://www.mdpi.com/1420-3049/28/18/6683 |
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