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Olefin Cross-Metathesis Reactions at Room Temperature Using the Nonionic Amphiphile “PTS”: Just Add Water†
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Section:Abstract
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.
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This article has been cited by 12 ACS Journal articles (5 most recent appear below).
TPGS-750-M: A Second-Generation Amphiphile for Metal-Catalyzed Cross-Couplings in Water at Room Temperature
Bruce H. Lipshutz, Subir Ghorai, Alexander R. Abela, Ralph Moser, Takashi Nishikata, Christophe Duplais, and Arkady Krasovskiy , Ricky D. Gaston and Robert C. GadwoodThe Journal of Organic Chemistry2011 76 (11), 4379-4391TPGS-750-M: A Second-Generation Amphiphile for Metal-Catalyzed Cross-Couplings in Water at Room Temperature
Bruce H. Lipshutz, Subir Ghorai, Alexander R. Abela, Ralph Moser, Takashi Nishikata, Christophe Duplais, and Arkady Krasovskiy , Ricky D. Gaston and Robert C. GadwoodThe Journal of Organic Chemistry2011 76 (11), 4379-4391An 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-...
Rate Enhanced Olefin Cross-Metathesis Reactions: The Copper Iodide Effect
Karl Voigtritter, Subir Ghorai, and Bruce H. LipshutzThe Journal of Organic Chemistry2011 76 (11), 4697-4702Rate Enhanced Olefin Cross-Metathesis Reactions: The Copper Iodide Effect
Karl Voigtritter, Subir Ghorai, and Bruce H. LipshutzThe Journal of Organic Chemistry2011 76 (11), 4697-4702Copper iodide has been shown to be an effective cocatalyst for the olefin cross-metathesis reaction. In particular, it has both a catalyst stabilizing effect due to iodide ion, as well as copper(I)-based phosphine-scavenging properties that apply to use ...
Manipulating Micellar Environments for Enhancing Transition Metal-Catalyzed Cross-Couplings in Water at Room Temperature
Bruce H. Lipshutz, Subir Ghorai, Wendy Wen Yi Leong, and Benjamin R. Taft , Daniel V. KrogstadThe Journal of Organic Chemistry2011 Article ASAPManipulating Micellar Environments for Enhancing Transition Metal-Catalyzed Cross-Couplings in Water at Room Temperature
Bruce H. Lipshutz, Subir Ghorai, Wendy Wen Yi Leong, and Benjamin R. Taft , Daniel V. KrogstadThe Journal of Organic Chemistry2011 Article ASAPThe 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 ...
Olefin Cross-Metathesis on Proteins: Investigation of Allylic Chalcogen Effects and Guiding Principles in Metathesis Partner Selection
Yuya A. Lin, Justin M. Chalker, and Benjamin G. DavisJournal of the American Chemical Society2010 132 (47), 16805-16811Olefin Cross-Metathesis on Proteins: Investigation of Allylic Chalcogen Effects and Guiding Principles in Metathesis Partner Selection
Yuya A. Lin, Justin M. Chalker, and Benjamin G. DavisJournal of the American Chemical Society2010 132 (47), 16805-16811Olefin metathesis has recently emerged as a viable reaction for chemical protein modification. The scope and limitations of olefin metathesis in bioconjugation, however, remain unclear. Herein we report an assessment of various factors that contribute to ...
Water: Nature’s Reaction Enforcer—Comparative Effects for Organic Synthesis “In-Water” and “On-Water”
Richard N. Butler and Anthony G. CoyneChemical Reviews2010 110 (10), 6302-6337Water: Nature’s Reaction Enforcer—Comparative Effects for Organic Synthesis “In-Water” and “On-Water”
Richard N. Butler and Anthony G. CoyneChemical Reviews2010 110 (10), 6302-6337
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- Published In Issue April 03, 2008
- Received January 6, 2008
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