1-(N-Acylamino)alkyltriarylphosphonium Salts with Weakened Cα-P+ Bond Strength—Synthetic Applications
The α-amidoalkylating properties of 1-(N-acylamino)alkyltriarylphosphonium salts with weakened Cα-P+ bond strength are discussed and examined. It is demonstrated that such type of phosphonium salts reacts smoothly with a diverse array of carbon- and heteroatom-based nucleophiles,...
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MDPI AG
2018-09-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/10/2453 |
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| author | Jakub Adamek Anna Węgrzyk Justyna Kończewicz Krzysztof Walczak Karol Erfurt |
| author_facet | Jakub Adamek Anna Węgrzyk Justyna Kończewicz Krzysztof Walczak Karol Erfurt |
| author_sort | Jakub Adamek |
| collection | DOAJ |
| description | The α-amidoalkylating properties of 1-(N-acylamino)alkyltriarylphosphonium salts with weakened Cα-P+ bond strength are discussed and examined. It is demonstrated that such type of phosphonium salts reacts smoothly with a diverse array of carbon- and heteroatom-based nucleophiles, including 1-morpholinocyclohexene, 1,3-dicarbonyl compounds, benzotriazole sodium salt, p-toluenesulfinate sodium salt, benzylamine, triarylphosphines, and other P-nucleophiles. Reactions are conducted at room temperature, in a short time (5–15 min) and mostly without catalysts. Simple work-up procedures result in good or very good yields of products. The structures of known compounds were established by spectroscopic methods and all new compounds have been fully characterized using 1H-, 13C-, 31P-NMR, IR spectroscopy, and high-resolution mass spectrometry. Mechanistic aspects of described transformations are also performed and discussed. It was demonstrated that unique properties make 1-(N-acylamino)alkyl-triarylphosphonium salts with weakened Cα-P+ bond strength interesting building blocks with great potential, especially in α-amidoalkylation reactions. |
| first_indexed | 2024-04-12T21:41:12Z |
| format | Article |
| id | doaj.art-88ec54a4ee2747cca3748c75f3777ca0 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-12T21:41:12Z |
| publishDate | 2018-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-88ec54a4ee2747cca3748c75f3777ca02022-12-22T03:15:46ZengMDPI AGMolecules1420-30492018-09-012310245310.3390/molecules23102453molecules231024531-(N-Acylamino)alkyltriarylphosphonium Salts with Weakened Cα-P+ Bond Strength—Synthetic ApplicationsJakub Adamek0Anna Węgrzyk1Justyna Kończewicz2Krzysztof Walczak3Karol Erfurt4Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, PolandDepartment of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, PolandThe α-amidoalkylating properties of 1-(N-acylamino)alkyltriarylphosphonium salts with weakened Cα-P+ bond strength are discussed and examined. It is demonstrated that such type of phosphonium salts reacts smoothly with a diverse array of carbon- and heteroatom-based nucleophiles, including 1-morpholinocyclohexene, 1,3-dicarbonyl compounds, benzotriazole sodium salt, p-toluenesulfinate sodium salt, benzylamine, triarylphosphines, and other P-nucleophiles. Reactions are conducted at room temperature, in a short time (5–15 min) and mostly without catalysts. Simple work-up procedures result in good or very good yields of products. The structures of known compounds were established by spectroscopic methods and all new compounds have been fully characterized using 1H-, 13C-, 31P-NMR, IR spectroscopy, and high-resolution mass spectrometry. Mechanistic aspects of described transformations are also performed and discussed. It was demonstrated that unique properties make 1-(N-acylamino)alkyl-triarylphosphonium salts with weakened Cα-P+ bond strength interesting building blocks with great potential, especially in α-amidoalkylation reactions.http://www.mdpi.com/1420-3049/23/10/2453organophosphorus chemistryphosphonium saltsα-amidoalkylating agentsN-acyliminium cationN-acylimine |
| spellingShingle | Jakub Adamek Anna Węgrzyk Justyna Kończewicz Krzysztof Walczak Karol Erfurt 1-(N-Acylamino)alkyltriarylphosphonium Salts with Weakened Cα-P+ Bond Strength—Synthetic Applications Molecules organophosphorus chemistry phosphonium salts α-amidoalkylating agents N-acyliminium cation N-acylimine |
| title | 1-(N-Acylamino)alkyltriarylphosphonium Salts with Weakened Cα-P+ Bond Strength—Synthetic Applications |
| title_full | 1-(N-Acylamino)alkyltriarylphosphonium Salts with Weakened Cα-P+ Bond Strength—Synthetic Applications |
| title_fullStr | 1-(N-Acylamino)alkyltriarylphosphonium Salts with Weakened Cα-P+ Bond Strength—Synthetic Applications |
| title_full_unstemmed | 1-(N-Acylamino)alkyltriarylphosphonium Salts with Weakened Cα-P+ Bond Strength—Synthetic Applications |
| title_short | 1-(N-Acylamino)alkyltriarylphosphonium Salts with Weakened Cα-P+ Bond Strength—Synthetic Applications |
| title_sort | 1 n acylamino alkyltriarylphosphonium salts with weakened cα p bond strength synthetic applications |
| topic | organophosphorus chemistry phosphonium salts α-amidoalkylating agents N-acyliminium cation N-acylimine |
| url | http://www.mdpi.com/1420-3049/23/10/2453 |
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