Synthetically versatile imidazolium chlorides, especially 1,3‐bis‐(2,6‐diisopropylphenyl)‐imidazolium chloride (IPrHCl) along with copper (I) iodide and cesium carbonate, were found to be useful to form C−O bonds via coupling of phenols and aryl/heteroaryl bromides. In this catalysis, the metal:ligand (Cu:IPr) loading was optimised to 1.0 mol%, making it an inexpensive and a simple one pot catalytic route for synthesising a variety of diaryl ethers. The catalytic cycle was probed by UV‐Vis, FT‐IR and HRMS techniques confirming involvement of a copper‐imidazolium‐carbonate complex.
Studies of environmentally benign catalytic methods are of great value in modern chemical synthesis, especially the chemo‐selective construction of chemical bonds under green conditions. This work elucidates such preferential synthesis of C−N bond over C−O bond via selective N‐arylation of 3‐aminophenols using 1,3‐bis‐[2‐hydroxyphenyl] imidazolium chloride (IHPHCl) and copper iodide as catalyst (1 mol %) in aqueous medium. Presence of chelating group (−OH) on IHPHCl enhances N‐selectivity. Overall this is a simple and green method for selective N‐arylation of 3‐aminophenols with good substrate scope and yields (60–88 %). GC‐MS, HRMS and other spectroscopic techniques were utilised in detailing the kinetics and mechanistic aspects.
A single step approach for the synthesis of non-symmetrical tetraaryl-α-diimines via the transimination route at room temperature was developed. The reported procedure was found to be an elegant route for making non-symmetrical tetraaryl-α-diimines, which upon cyclization yields a series of new non-symmetrical 1,3,4,5-tetraarylimidazolium chlorides, as stable N-heterocyclic carbene (NHC) precursors.
As solutes in carbon tetrachloride at 25". allyl chloride. bromide, and iodide have molar Kerr constants ( x10l2) of 48.2.96.6, and 99.1 .and dipole moments (D) of 1-75.1.73. and 1.56. respectively. When the anisotropic carbonhalogen bond polarisabilities previously found applicable to ethyl and isopropyl halides are used, the new measurements are reconcilable with the non-planar conformations specified by Bowen, Gilchrist, and Sutton, but not with mixtures of s-cisand s-trans-conformers alone. Attempts to predict average molar Kerr constants, by assuming hindered internal rotations to be due to van der Waals and dipole-induced dipole interactions, are also described.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.