β-Ketoallylic methylsulfones synthesis via inert C(sp 3)–H bond activation by magnetic Ag–Cu MOF
Abstract Herein, the one-pot tandem synthesis of β-ketoallylic methylsulfones has been achieved from readily available dimethyl sulfoxide and acetophenones as coupling partners in one step. In this procedure, dimethyl sulfoxide serves as a triple role including solvent, dual synthon and as an oxidan...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2023-12-01
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| Series: | Scientific Reports |
| Online Access: | https://doi.org/10.1038/s41598-023-49670-5 |
| _version_ | 1797377079237410816 |
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| author | Firouz Matloubi Moghaddam Atefeh Jarahiyan Parisa Yaqubnezhad Pazoki |
| author_facet | Firouz Matloubi Moghaddam Atefeh Jarahiyan Parisa Yaqubnezhad Pazoki |
| author_sort | Firouz Matloubi Moghaddam |
| collection | DOAJ |
| description | Abstract Herein, the one-pot tandem synthesis of β-ketoallylic methylsulfones has been achieved from readily available dimethyl sulfoxide and acetophenones as coupling partners in one step. In this procedure, dimethyl sulfoxide serves as a triple role including solvent, dual synthon and as an oxidant agent. The use of magnetic Ag–Cu MOF as a bimetallic catalyst is the key to the progress of the reaction due to its accessible active sites. It provides facile access to various β-ketoallylic methylsulfone derivatives from direct C(sp 3)–H bond activation and functionalization of aromatic methyl ketones especially acetophenones with electron-rich and electron-poor groups. Moreover, the present work offers a synthetically powerful strategy to form products in good to excellent yields (74–96%) with the atom, step, and pot economics. It has also delivered a new chromane-4-one derivative from 2-hydroxy acetophenone with intramolecular Michael-addition of related β-ketoallyl methylsulfone product. In the final step, the electronic properties of some products have been predicted with the theoretical studies. |
| first_indexed | 2024-03-08T19:47:49Z |
| format | Article |
| id | doaj.art-e3bde79a362b4e1b9d2baa56d24e6a39 |
| institution | Directory Open Access Journal |
| issn | 2045-2322 |
| language | English |
| last_indexed | 2024-03-08T19:47:49Z |
| publishDate | 2023-12-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj.art-e3bde79a362b4e1b9d2baa56d24e6a392023-12-24T12:16:26ZengNature PortfolioScientific Reports2045-23222023-12-0113111610.1038/s41598-023-49670-5β-Ketoallylic methylsulfones synthesis via inert C(sp 3)–H bond activation by magnetic Ag–Cu MOFFirouz Matloubi Moghaddam0Atefeh Jarahiyan1Parisa Yaqubnezhad Pazoki2Laboratory of Organic Synthesis and Natural Products, Department of Chemistry, Sharif University of TechnologyLaboratory of Organic Synthesis and Natural Products, Department of Chemistry, Sharif University of TechnologyLaboratory of Organic Synthesis and Natural Products, Department of Chemistry, Sharif University of TechnologyAbstract Herein, the one-pot tandem synthesis of β-ketoallylic methylsulfones has been achieved from readily available dimethyl sulfoxide and acetophenones as coupling partners in one step. In this procedure, dimethyl sulfoxide serves as a triple role including solvent, dual synthon and as an oxidant agent. The use of magnetic Ag–Cu MOF as a bimetallic catalyst is the key to the progress of the reaction due to its accessible active sites. It provides facile access to various β-ketoallylic methylsulfone derivatives from direct C(sp 3)–H bond activation and functionalization of aromatic methyl ketones especially acetophenones with electron-rich and electron-poor groups. Moreover, the present work offers a synthetically powerful strategy to form products in good to excellent yields (74–96%) with the atom, step, and pot economics. It has also delivered a new chromane-4-one derivative from 2-hydroxy acetophenone with intramolecular Michael-addition of related β-ketoallyl methylsulfone product. In the final step, the electronic properties of some products have been predicted with the theoretical studies.https://doi.org/10.1038/s41598-023-49670-5 |
| spellingShingle | Firouz Matloubi Moghaddam Atefeh Jarahiyan Parisa Yaqubnezhad Pazoki β-Ketoallylic methylsulfones synthesis via inert C(sp 3)–H bond activation by magnetic Ag–Cu MOF Scientific Reports |
| title | β-Ketoallylic methylsulfones synthesis via inert C(sp 3)–H bond activation by magnetic Ag–Cu MOF |
| title_full | β-Ketoallylic methylsulfones synthesis via inert C(sp 3)–H bond activation by magnetic Ag–Cu MOF |
| title_fullStr | β-Ketoallylic methylsulfones synthesis via inert C(sp 3)–H bond activation by magnetic Ag–Cu MOF |
| title_full_unstemmed | β-Ketoallylic methylsulfones synthesis via inert C(sp 3)–H bond activation by magnetic Ag–Cu MOF |
| title_short | β-Ketoallylic methylsulfones synthesis via inert C(sp 3)–H bond activation by magnetic Ag–Cu MOF |
| title_sort | β ketoallylic methylsulfones synthesis via inert c sp 3 h bond activation by magnetic ag cu mof |
| url | https://doi.org/10.1038/s41598-023-49670-5 |
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