Michael addition of P-nucleophiles to azoalkenes provides simple access to phosphine oxides bearing an alkylhydrazone moiety Full article
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Frontiers in Chemistry
ISSN: 2296-2646 |
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| Output data | Year: 2023, Volume: 11, Article number : 1177680, Pages count : DOI: 10.3389/fchem.2023.1177680 | ||
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Abstract:
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.
Cite:
Kokuev A.O.
, Sukhorukov A.Y.
Michael addition of P-nucleophiles to azoalkenes provides simple access to phosphine oxides bearing an alkylhydrazone moiety
Frontiers in Chemistry. 2023. V.11. 1177680 . DOI: 10.3389/fchem.2023.1177680 WOS Scopus OpenAlex
Michael addition of P-nucleophiles to azoalkenes provides simple access to phosphine oxides bearing an alkylhydrazone moiety
Frontiers in Chemistry. 2023. V.11. 1177680 . DOI: 10.3389/fchem.2023.1177680 WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:000979041800001 |
| Scopus: | 2-s2.0-85153753804 |
| OpenAlex: | W4365455454 |