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. 2023 Dec 19;29(1):18.
doi: 10.3390/molecules29010018.

1-Hydroxyalkylphosphonium Salts-Synthesis and Properties

Jakub Adamek  1   2 , Anna Kuźnik  1   2 , Agnieszka Październiok-Holewa  1   2 , Mirosława Grymel  1   2 , Dominika Kozicka  1   2 , Dominika Mierzwa  1 , Karol Erfurt  3
Affiliations

1-Hydroxyalkylphosphonium Salts-Synthesis and Properties

Jakub Adamek et al. Molecules. .

Abstract

An efficient and convenient method for the synthesis of 1-hydroxyalkylphosphonium salts is described. Reactions were carried out at room temperature, in a short time, and without chromatography for product isolation. The properties of the obtained phosphonium salts were examined and discussed. In this paper, primary attention was paid to the stability of phosphonium salts, depending on the structure of the aldehydes used as substrates in their preparation. Other conditions such as the type of solvent, temperature, and molar ratio of the substrates were also investigated. Finally, the high reactivity of 1-hydroxyalkylphosphonium salts was demonstrated in reactions with amide-type substrates and (hetero)aromatic compounds. The developed step-by-step procedure (with the isolation of 1-hydroxyphosphonium salts) was compared to the one-pot protocol (in situ formation of such phosphonium salts).

Keywords: alkylating agent; alkylation; phosphonium salts; stability; synthesis.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
1-hydroxyalkylphosphonium salts 1: synthesis and applications.
Scheme 2
Scheme 2
Hydroxyalkylphosphonium salts from bromomalonaldehyde (A) or (E)-cinnamaldehyde (B): conditions and results.
Figure 1
Figure 1
31P{1H} NMR spectra (162 MHz/CD3CN) of reaction mixtures (1-naphthaldehyde with triphenylphosphonium tetrafluoroborate) recorded at 25 °C, 35 °C, 45 °C, and back to 25 °C.
Scheme 3
Scheme 3
Conditions and results for the reaction of 1-hydroxyalkylphosphonium salts 1 with (hetero)aromatic compounds (step-by-step vs. one-pot protocol).
Scheme 4
Scheme 4
Conditions and results for the reaction of 1-hydroxyalkylphosphonium salts 1 with amide-type substrates.
Scheme 5
Scheme 5
The reaction of 1-hydroxyalkylphosphonium salts 1a and 1o with acrylamide—possible pathways.
See this image and copyright information in PMC

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