Michael addition of P-nucleophiles to azoalkenes provides simple access to phosphine oxides bearing an alkylhydrazone moiety
β-Hydrazonophosphine oxides are precursors of useful organophosphorus compounds, including phosphorylated N-heterocycles, α-aminophosphonates, and vinylphosphonates. In this work, a general transition metal-free synthesis of β-hydrazonophosphine oxides was developed. The method relies on the Michael...
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2023-04-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fchem.2023.1177680/full |
| _version_ | 1797847641770426368 |
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| author | Alexandr O. Kokuev Alexey Yu. Sukhorukov |
| author_facet | Alexandr O. Kokuev Alexey Yu. Sukhorukov |
| author_sort | Alexandr O. Kokuev |
| collection | DOAJ |
| description | β-Hydrazonophosphine oxides are precursors of useful organophosphorus compounds, including phosphorylated N-heterocycles, α-aminophosphonates, and vinylphosphonates. In this work, a general transition metal-free synthesis of β-hydrazonophosphine oxides was developed. The method relies on the Michael addition of phosphine oxides R2P(O)H to reactive azoalkenes (1,2-diaza-1,3-butadienes), which are generated in situ from α-halohydrazones and Hunig’s base. The reaction stereoselectively leads to Z-isomers of β-hydrazonophosphine oxides that are stabilized by intramolecular hydrogen bonding. The conversion of the products thus obtained into potential chelating ligands was showcased. |
| first_indexed | 2024-04-09T18:15:51Z |
| format | Article |
| id | doaj.art-95ea523d2c6a4f7a96774fb92abba408 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-04-09T18:15:51Z |
| publishDate | 2023-04-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-95ea523d2c6a4f7a96774fb92abba4082023-04-13T04:53:38ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462023-04-011110.3389/fchem.2023.11776801177680Michael addition of P-nucleophiles to azoalkenes provides simple access to phosphine oxides bearing an alkylhydrazone moietyAlexandr O. KokuevAlexey Yu. Sukhorukovβ-Hydrazonophosphine oxides are precursors of useful organophosphorus compounds, including phosphorylated N-heterocycles, α-aminophosphonates, and vinylphosphonates. In this work, a general transition metal-free synthesis of β-hydrazonophosphine oxides was developed. The method relies on the Michael addition of phosphine oxides R2P(O)H to reactive azoalkenes (1,2-diaza-1,3-butadienes), which are generated in situ from α-halohydrazones and Hunig’s base. The reaction stereoselectively leads to Z-isomers of β-hydrazonophosphine oxides that are stabilized by intramolecular hydrogen bonding. The conversion of the products thus obtained into potential chelating ligands was showcased.https://www.frontiersin.org/articles/10.3389/fchem.2023.1177680/fullorganophosphorus compoundsphosphine oxidesazoalkenesMichael additionhydrazonesreactive intermediates |
| spellingShingle | Alexandr O. Kokuev Alexey Yu. Sukhorukov Michael addition of P-nucleophiles to azoalkenes provides simple access to phosphine oxides bearing an alkylhydrazone moiety Frontiers in Chemistry organophosphorus compounds phosphine oxides azoalkenes Michael addition hydrazones reactive intermediates |
| title | Michael addition of P-nucleophiles to azoalkenes provides simple access to phosphine oxides bearing an alkylhydrazone moiety |
| title_full | Michael addition of P-nucleophiles to azoalkenes provides simple access to phosphine oxides bearing an alkylhydrazone moiety |
| title_fullStr | Michael addition of P-nucleophiles to azoalkenes provides simple access to phosphine oxides bearing an alkylhydrazone moiety |
| title_full_unstemmed | Michael addition of P-nucleophiles to azoalkenes provides simple access to phosphine oxides bearing an alkylhydrazone moiety |
| title_short | Michael addition of P-nucleophiles to azoalkenes provides simple access to phosphine oxides bearing an alkylhydrazone moiety |
| title_sort | michael addition of p nucleophiles to azoalkenes provides simple access to phosphine oxides bearing an alkylhydrazone moiety |
| topic | organophosphorus compounds phosphine oxides azoalkenes Michael addition hydrazones reactive intermediates |
| url | https://www.frontiersin.org/articles/10.3389/fchem.2023.1177680/full |
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