Nucleophilic Aromatic Substitution Reactions in Water Enabled by Micellar Catalysis
2015
Isley, Nicholas A. | Linstadt, Roscoe T. H. | Kelly, Sean M. | Gallou, Fabrice | Lipshutz, Bruce H.
Given the huge dependence on dipolar, aprotic solvents such as DMF, DMSO, DMAc, and NMP in nucleophilic aromatic substitution reactions (SNAr), a simple and environmentally friendly alternative is reported. Use of a “benign-by-design” nonionic surfactant, TPGS-750-M, in water enables nitrogen, oxygen, and sulfur nucleophiles to participate in SNAr reactions. Aromatic and heteroaromatic substrates readily participate in this micellar catalysis, which takes place at or near ambient temperatures.
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