ArticleBeilstein journal of organic chemistry2020
The McKenna reaction - avoiding side reactions in phosphonate deprotection.
Article in Beilstein journal of organic chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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5 citing papers in PubMed, 24 citations in OpenAlex.
- Relaxivity Modulation of Gd-HPDO3A-like Complexes by Introducing Polar and Protic Peripheral Groups.Molecules (Basel, Switzerland) · 2024Article
- Design, Synthesis, and Biological Evaluation of Small-Molecule-Based Radioligands with Improved Pharmacokinetic Properties for Imaging of Programmed Death Ligand 1.Journal of medicinal chemistry · 2023Article
- Exploring Hydrophilic PD-L1 Radiotracers Utilizing Phosphonic Acids: Insights into Unforeseen Pharmacokinetics.International journal of molecular sciences · 2023Article
- Sustainable Triazine-Based Dehydro-Condensation Agents for Amide Synthesis.Molecules (Basel, Switzerland) · 2021Article
- Synthesis of the 6-Substituted Imidazo[1,2-a]Pyridine-3-yl-2- Phosphonopropionic Acids as Potential Inhibitors of Rab Geranylgeranyl Transferase.Frontiers in chemistry · 2020Article
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5 authors at 1 institution in 1 country.
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Abstract
The McKenna reaction is a well-known and popular method for the efficient and mild synthesis of organophosphorus acids. Bromotrimethylsilane (BTMS) is the main reagent in this reaction, which transforms dialkyl phosphonate esters into bis(trimethylsilyl)esters, which are then easily converted into the target acids. However, the versatile character of the McKenna reaction is not always used to its full extent, due to formation of side products. Herein, demonstrated by using model examples we have not only analyzed the typical side processes accompanying the McKenna reaction, but also uncovered new ones. Further, we discovered that some commonly recommended precautions did not always circumvent the side reactions. The proposed results and recommendations may facilitate the synthesis of phosphonic acids.
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