title: Nucleophilic Aromatic Substitution Reactions in Water Enabled by Micellar Catalysis.
abstract: 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.
authors.affiliation: Department of Chemistry & Biochemistry, University of California , Santa Barbara, California 93106, United States.
authors.forename: Nicholas A
authors.initials: NA
authors.lastname: Isley
authors.affiliation: Department of Chemistry & Biochemistry, University of California , Santa Barbara, California 93106, United States.
authors.forename: Roscoe T H
authors.initials: RT
authors.lastname: Linstadt
authors.affiliation: Department of Chemistry & Biochemistry, University of California , Santa Barbara, California 93106, United States.
authors.forename: Sean M
authors.initials: SM
authors.lastname: Kelly
authors.affiliation: Chemical & Analytical Development, Novartis Pharma AG , 4056 Basel, Switzerland.
authors.forename: Fabrice
authors.initials: F
authors.lastname: Gallou
authors.affiliation: Department of Chemistry & Biochemistry, University of California , Santa Barbara, California 93106, United States.
authors.forename: Bruce H
authors.initials: BH
authors.lastname: Lipshutz
mesh_terms: D002384:Catalysis; D008823:Micelles; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D012997:Solvents; D013455:Sulfur / Q000737:chemistry; D013501:Surface-Active Agents; D014867:Water / Q000737:chemistry*
chemical_list: D008823:Micelles; D012997:Solvents; D013501:Surface-Active Agents; D014867:Water; D013455:Sulfur; D009584:Nitrogen; D010100:Oxygen