TPGS-750-M: A Second-Generation Amphiphile for Metal-Catalyzed Cross-Couplings in Water at Room Temperature
- 9 May 2011
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 76 (11), 4379-4391
- https://doi.org/10.1021/jo101974u
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.Keywords
This publication has 56 references indexed in Scilit:
- Cationic Palladium(II) Catalysis: C−H Activation/Suzuki−Miyaura Couplings at Room TemperatureJournal of the American Chemical Society, 2010
- Room Temperature C-H Activation and Cross‐Coupling of Aryl Ureas in WaterAngewandte Chemie, 2010
- Pd-Catalyzed Synthesis of Allylic Silanes from Allylic EthersOrganic Letters, 2009
- Zn-Mediated, Pd-Catalyzed Cross-Couplings in Water at Room Temperature Without Prior Formation of Organozinc ReagentsJournal of the American Chemical Society, 2009
- Aminations of Aryl Bromides in Water at Room TemperatureAdvanced Synthesis & Catalysis, 2009
- Allylic Ethers as Educts for Suzuki−Miyaura Couplings in Water at Room TemperatureJournal of the American Chemical Society, 2009
- Palladium(II)‐Catalyzed C-H Activation/C-C Cross‐Coupling Reactions: Versatility and PracticalityAngewandte Chemie, 2009
- Palladium- and Copper-Catalyzed Arylation of Carbon−Hydrogen BondsAccounts of Chemical Research, 2009
- Rhodium-Catalyzed C−C Bond Formation via Heteroatom-Directed C−H Bond ActivationChemical Reviews, 2009
- Amination of Allylic Alcohols in Water at Room TemperatureOrganic Letters, 2009