Scope and Mechanistic Limitations of a Sonogashira Coupling Reaction on an Imidazole Backbone was written by Sandtorv, Alexander H.;Bjorsvik, Hans-Rene. And the article was included in European Journal of Organic Chemistry in 2015.Category: iodides-buliding-blocks This article mentions the following:
A Sonogashira coupling reaction method to join terminal alkynes to the imidazole backbone was developed and studied. The method exhibits good functional group tolerance and provides target 4-alkynylated imidazoles in 70-93% yield. The alkyne reagents were characterized by DFT calculations, from which electrostatic potential surfaces (EPS) were produced. A clear correlation between the EPS of the triple bond and the success of the coupling reaction was revealed. If the EPS is in range -94 to -105 kJ mol-1 the coupling is successful. An unsuccessful class of reagents (alkynols) was made compatible by an auxiliary group (tert-butyldimethylsilyl). EPSs of these modified reagents then resembled those of the model and these auxiliary-assisted reagents then coupled successfully in excellent yields. In the experiment, the researchers used many compounds, for example, 4,5-Diiodo-1H-imidazole (cas: 15813-09-9Category: iodides-buliding-blocks).
4,5-Diiodo-1H-imidazole (cas: 15813-09-9) belongs to iodide derivatives. Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics. A typical method for synthesis of aromatic iodides is diazotization of primary aromatic amines followed by treatment of potassium iodide. Aliphatic alcohols are converted to alkyl iodides by treating with hydrogen iodide.Category: iodides-buliding-blocks
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com