1019646-02-6Relevant articles and documents
Manipulating micellar environments for enhancing transition metal-catalyzed cross-couplings in water at room temperature
Lipshutz, Bruce H.,Ghorai, Subir,Leong, Wendy Wen Yi,Taft, Benjamin R.,Krogstad, Daniel V.
experimental part, p. 5061 - 5073 (2011/08/06)
The remarkable effects of added salts on the properties of aqueous micelles derived from the amphiphile PTS are described. Most notably, Heck reactions run in the presence of NaCl lead to couplings on aryl bromides in water at room temperature. Olefin cross- and ring-closing metathesis reactions run in the presence of small amounts of pH-lowering KHSO4 are also accelerated, another phenomenon that does not apply to typical processes in organic media. These salt effects allow, in general, for synthetically valuable C-C bond-forming processes to be conducted under environmentally benign conditions. Recycling of the surfactant is also demonstrated.
Olefin cross-metathesis reactions at room temperature using the nonionic amphiphile "PTS": Just add water
Lipshutz, Bruce H.,Aguinaldo, Grant T.,Ghorai, Subir,Voigtritter, Karl
supporting information; experimental part, p. 1325 - 1328 (2009/04/10)
(Chemical Equation Presented) The first examples of unsymmetrical olefin cross-metathesis reactions in water, involving water-insoluble substrates, at room temperature and using commercially available catalysts are reported. The key to success is to include small percentages of the nonionic, vitamin E-based amphiphile "PTS". The nanometer micelles formed accommodate water-insoluble substrates, along with a readily available Ru-based metathesis catalyst. Reactions proceed at ambient temperatures with high efficiency and very high E-selectivity, and products are easily isolated.