Novel nucleophilic addition SN2'–SN2' pathway: utilizing phosphonium salts as electrophilic agents for synthesizing new phosphine oxides of Morita–Baylis–Hillman (MBH) adducts
An efficient and practical approach has been developed for synthesizing phosphonates and phosphine oxides from Morita–Baylis–Hillman (MBH) adducts through the alkylation of trialkylphosphites and ethoxydiphenylphosphine using phosphonium salts derived from MBH as powerful alkylating agents.The alkyl...
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Académie des sciences
2024-12-01
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| Series: | Comptes Rendus. Chimie |
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| Online Access: | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.349/ |
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| author | Elleuch, Haitham Yaccoubi, Ferid Ayari, Sami Saadi, Fatma |
| author_facet | Elleuch, Haitham Yaccoubi, Ferid Ayari, Sami Saadi, Fatma |
| author_sort | Elleuch, Haitham |
| collection | DOAJ |
| description | An efficient and practical approach has been developed for synthesizing phosphonates and phosphine oxides from Morita–Baylis–Hillman (MBH) adducts through the alkylation of trialkylphosphites and ethoxydiphenylphosphine using phosphonium salts derived from MBH as powerful alkylating agents.The alkylation proceeds via a Michaelis–Arbuzov mechanism. This regiospecific reaction combining the SN2' + SN2' = SN2 pathway was conducted under refluxing in CHCl3, resulting in the isolation of the products in good yields. |
| format | Article |
| id | doaj-art-69c2b23f3ffa4c5bbe43d3066721c526 |
| institution | Kabale University |
| issn | 1878-1543 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Académie des sciences |
| record_format | Article |
| series | Comptes Rendus. Chimie |
| spelling | doaj-art-69c2b23f3ffa4c5bbe43d3066721c5262025-02-07T13:39:46ZengAcadémie des sciencesComptes Rendus. Chimie1878-15432024-12-0127G126927910.5802/crchim.34910.5802/crchim.349Novel nucleophilic addition SN2'–SN2' pathway: utilizing phosphonium salts as electrophilic agents for synthesizing new phosphine oxides of Morita–Baylis–Hillman (MBH) adductsElleuch, Haitham0https://orcid.org/0000-0003-2373-6427Yaccoubi, Ferid1https://orcid.org/0000-0002-2672-1442Ayari, Sami2https://orcid.org/0000-0002-1505-1922Saadi, Fatma3https://orcid.org/0000-0001-9587-4736Laboratory of Structural Organic Chemistry and Macromolecular, LR99ES14, Faculty of Sciences of Tunis, University of Tunis El Manar, University Campus, 2092 Tunis, TunisiaDepartment of Chemistry, Faculty of Science and Humanity Studies at Al Quwayiyah, Shaqra University, Al-Quwayiyah 19245, Saudi Arabia; Laboratory of Structural Organic Chemistry and Macromolecular, LR99ES14, Faculty of Sciences of Tunis, University of Tunis El Manar, University Campus, 2092 Tunis, TunisiaLaboratory of Microorganisms and Active Biomolecules, LR03ES03, Department of Biology, Faculty of Sciences of Tunis, University of Tunis-El Manar, 2092 El Manar I Tunis, TunisiaDepartment of Chemistry, Faculty of Science, Northern Border University, Arar, Kingdom of Saudi ArabiaAn efficient and practical approach has been developed for synthesizing phosphonates and phosphine oxides from Morita–Baylis–Hillman (MBH) adducts through the alkylation of trialkylphosphites and ethoxydiphenylphosphine using phosphonium salts derived from MBH as powerful alkylating agents.The alkylation proceeds via a Michaelis–Arbuzov mechanism. This regiospecific reaction combining the SN2' + SN2' = SN2 pathway was conducted under refluxing in CHCl3, resulting in the isolation of the products in good yields.https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.349/PhosphonatesPhosphine oxideMBH adductsAlkylationMichaelis–Arbuzov |
| spellingShingle | Elleuch, Haitham Yaccoubi, Ferid Ayari, Sami Saadi, Fatma Novel nucleophilic addition SN2'–SN2' pathway: utilizing phosphonium salts as electrophilic agents for synthesizing new phosphine oxides of Morita–Baylis–Hillman (MBH) adducts Comptes Rendus. Chimie Phosphonates Phosphine oxide MBH adducts Alkylation Michaelis–Arbuzov |
| title | Novel nucleophilic addition SN2'–SN2' pathway: utilizing phosphonium salts as electrophilic agents for synthesizing new phosphine oxides of Morita–Baylis–Hillman (MBH) adducts |
| title_full | Novel nucleophilic addition SN2'–SN2' pathway: utilizing phosphonium salts as electrophilic agents for synthesizing new phosphine oxides of Morita–Baylis–Hillman (MBH) adducts |
| title_fullStr | Novel nucleophilic addition SN2'–SN2' pathway: utilizing phosphonium salts as electrophilic agents for synthesizing new phosphine oxides of Morita–Baylis–Hillman (MBH) adducts |
| title_full_unstemmed | Novel nucleophilic addition SN2'–SN2' pathway: utilizing phosphonium salts as electrophilic agents for synthesizing new phosphine oxides of Morita–Baylis–Hillman (MBH) adducts |
| title_short | Novel nucleophilic addition SN2'–SN2' pathway: utilizing phosphonium salts as electrophilic agents for synthesizing new phosphine oxides of Morita–Baylis–Hillman (MBH) adducts |
| title_sort | novel nucleophilic addition sn2 sn2 pathway utilizing phosphonium salts as electrophilic agents for synthesizing new phosphine oxides of morita baylis hillman mbh adducts |
| topic | Phosphonates Phosphine oxide MBH adducts Alkylation Michaelis–Arbuzov |
| url | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.349/ |
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