1346557-06-9Relevant academic research and scientific papers
Phase separation as a strategy toward controlling dilution effects in macrocyclic glaser-hay couplings
Bedard, Anne-Catherine,Collins, Shawn K.
, p. 19976 - 19981 (2012/01/13)
Macrocycles are abundant in numerous chemical applications, however the traditional strategy for the preparation of these compounds remains cumbersome and environmentally damaging; involving tedious reaction set-ups and extremely dilute reaction media. The development of a macrocyclization strategy conducted at high concentrations is described which exploits phase separation of the catalyst and substrate, as a strategy to control dilution effects. Sequestering a copper catalyst in a highly polar and/or hydrophilic phase can be achieved using a hydrophilic ligand, T-PEG1900, a PEGylated TMEDA derivative. Similarly, phase separation is possible when suitable copper complexes are soluble in PEG400, a green and efficient solvent which can be utilized in biphasic mixtures for promoting macrocyclization at high concentrations. The latter phase separation technique can be exploited for the synthesis of a wide range of industrially relevant macrocycles with varying ring sizes and functional groups.
