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Open AccessArticle

1-(N-Acylamino)alkyltriarylphosphonium Salts with Weakened Cα-P+ Bond Strength—Synthetic Applications

1
Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, Poland
2
Biotechnology Center of Silesian University of Technology, B. Krzywoustego 8, 44-100 Gliwice, Poland
3
Department of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, Poland
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(10), 2453; https://doi.org/10.3390/molecules23102453
Received: 31 August 2018 / Revised: 19 September 2018 / Accepted: 23 September 2018 / Published: 25 September 2018
(This article belongs to the Special Issue Organophosphorus Chemistry 2018)
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. View Full-Text
Keywords: organophosphorus chemistry; phosphonium salts; α-amidoalkylating agents; N-acyliminium cation; N-acylimine organophosphorus chemistry; phosphonium salts; α-amidoalkylating agents; N-acyliminium cation; N-acylimine
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MDPI and ACS Style

Adamek, J.; Węgrzyk, A.; Kończewicz, J.; Walczak, K.; Erfurt, K. 1-(N-Acylamino)alkyltriarylphosphonium Salts with Weakened Cα-P+ Bond Strength—Synthetic Applications. Molecules 2018, 23, 2453.

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