The electrochemically-assisted synthesis of (hetero)arylphosphonates from (hetero)aryl halides and dimethyl phosphite is described. Very mild and simple conditions are employed as the cross-coupling is carried out in galvanostatic mode, in an undivided cell at room temperature, using NiBr2bpy as the easily available pre-catalyst and acetonitrile as the solvent. In addition, both aryl bromides and iodides can be used as well, providing the corresponding (hetero)arylphosphonates in generally good yields. A mechanism involving the in situ generation of a Ni ate complex is proposed.
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http://dx.doi.org/10.1039/c8ob00500a | DOI Listing |
Molecules
August 2024
Division of Organic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland.
This review focuses on optical properties of compounds in which at least one phosphonate group is directly attached to a heteroaromatic ring. Additionally, the synthesis and other applications of these compounds are addressed in this work. The influence of the phosphonate substituent on the properties of the described compounds is discussed and compared with other non-phosphorus substituents, with particular attention given to photophysical properties, such as UV-Vis absorption and emission, fluorescence quantum yield and fluorescence lifetime.
View Article and Find Full Text PDFOrg Biomol Chem
June 2018
Électrochimie et Synthèse Organique, Université Paris Est, ICMPE (UMR 7182), CNRS, UPEC, F-94320 Thiais, France.
The electrochemically-assisted synthesis of (hetero)arylphosphonates from (hetero)aryl halides and dimethyl phosphite is described. Very mild and simple conditions are employed as the cross-coupling is carried out in galvanostatic mode, in an undivided cell at room temperature, using NiBr2bpy as the easily available pre-catalyst and acetonitrile as the solvent. In addition, both aryl bromides and iodides can be used as well, providing the corresponding (hetero)arylphosphonates in generally good yields.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!