title: Manipulating micellar environments for enhancing transition metal-catalyzed cross-couplings in water at room temperature.
abstract: 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 KHSO(4) 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.
authors.affiliation: Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, USA. lipshutz@chem.ucsb.edu
authors.forename: Bruce H
authors.initials: BH
authors.lastname: Lipshutz
authors.forename: Subir
authors.initials: S
authors.lastname: Ghorai
authors.forename: Wendy Wen Yi
authors.initials: WW
authors.lastname: Leong
authors.forename: Benjamin R
authors.initials: BR
authors.lastname: Taft
authors.forename: Daniel V
authors.initials: DV
authors.lastname: Krogstad
mesh_terms: D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D008823:Micelles; D046529:Microscopy, Electron, Transmission; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013696:Temperature; D014867:Water / Q000737:chemistry
chemical_list: D000475:Alkenes; D008823:Micelles; D014867:Water; D010165:Palladium