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| Format: | Artículo Open Access |
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Wiley
2025
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| Online-Zugang: | https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cssc.202500679 |
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Inhaltsangabe:
- Modular, Tricomponent, and Concurrent One‐Pot Synthesis of Libraries of γ‐Keto Sulfones and γ‐Keto Phosphine Oxides using Brønsted Acidic Eutectic Mixtures Marina Ramos‐Martín Joaquín García‐Álvarez Alejandro Presa Soto ChemSusChem A modular, three‐component, and sustainable one‐pot/one‐step protocol has been developed for the efficient and regioselective synthesis of libraries of γ‐keto sulfones and γ‐keto phosphine oxides through concurrent CC and CX bond formation (X = S or P). The acidic eutectic mixture ChCl/p‐TSA·H2O (1:2) (ChCl = choline chloride; p‐TSA = p‐toluenesulfonic acid) serves as both promoter and reaction medium. This transformation involves a cascade process comprising three consecutive steps: i) hydration of terminal alkynes to methyl ketones; ii) Claisen–Schmidt condensation with aldehydes, and iii) sulfa‐Michael or phospha‐Michael additions using sodium sulfinates or secondary phosphine oxides, respectively. The methodology provides high yields (up to 99%), excellent atom economy, and operational simplicity, as the products are isolated without the use of any toxic volatile organic solvents or tedious chromatographic purification. Its modular nature accommodates a broad range of substrates, including electron‐rich and electron‐deficient components, demonstrating robustness and versatility (112 examples). Furthermore, the protocol enables scalable (tenfold) and recyclable (five cycles) synthesis of biologically relevant γ‐keto derivatives under green conditions (E‐factor ≤ 10), offering a general strategy for sustainable and modular CC and CX bond‐forming reactions. 10.1002/cssc.202500679 http://creativecommons.org/licenses/by-nc-nd/4.0/