title: TPGS-750-M: a second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature.
abstract: An environmentally benign surfactant (TPGS-750-M), a diester composed of racemic α-tocopherol, MPEG-750, and succinic acid, has been designed and readily prepared as an effective nanomicelle-forming species for general use in metal-catalyzed cross-coupling reactions in water. Several "name" reactions, including Heck, Suzuki-Miyaura, Sonogashira, and Negishi-like couplings, have been studied using this technology, as have aminations, C-H activations, and olefin metathesis reactions. Physical data in the form of DLS and cryo-TEM measurements suggest that particle size and shape are key elements in achieving high levels of conversion and, hence, good isolated yields of products. This new amphiphile will soon be commercially available.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States. 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: Alexander R
authors.initials: AR
authors.lastname: Abela
authors.forename: Ralph
authors.initials: R
authors.lastname: Moser
authors.forename: Takashi
authors.initials: T
authors.lastname: Nishikata
authors.forename: Christophe
authors.initials: C
authors.lastname: Duplais
authors.forename: Arkady
authors.initials: A
authors.lastname: Krasovskiy
authors.forename: Ricky D
authors.initials: RD
authors.lastname: Gaston
authors.forename: Robert C
authors.initials: RC
authors.lastname: Gadwood
mesh_terms: D002384:Catalysis; D057927:Hydrophobic and Hydrophilic Interactions; D008670:Metals / Q000737:chemistry*; D008823:Micelles; D011092:Polyethylene Glycols; D013386:Succinates / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry; D013501:Surface-Active Agents / Q000737:chemistry; D013696:Temperature; D013830:Thiadiazoles / Q000737:chemistry; D014810:Vitamin E / Q000031:analogs & derivatives* / Q000737:chemistry; D014867:Water / Q000737:chemistry*
chemical_list: C448310:2-(3-phenylpropionylamino)-1,3,4-thiadiazole-5-sulfonamide; D008670:Metals; D008823:Micelles; D013386:Succinates; D013449:Sulfonamides; D013501:Surface-Active Agents; D013830:Thiadiazoles; D014867:Water; D014810:Vitamin E; D011092:Polyethylene Glycols; C014225:tocophersolan