TPGS-750-M: a second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature.

The Journal of organic chemistry (2011-05-10)
Bruce H Lipshutz, Subir Ghorai, Alexander R Abela, Ralph Moser, Takashi Nishikata, Christophe Duplais, Arkady Krasovskiy, Ricky D Gaston, Robert C Gadwood
RESUMEN

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.

MATERIALES
Referencia del producto
Marca
Descripción del producto

Sigma-Aldrich
DL-α-Tocopherol methoxypolyethylene glycol succinate solution, 2 wt. % in H2O
Sigma-Aldrich
DL-α-Tocopherol methoxypolyethylene glycol succinate solution, 5 wt. % in H2O
Sigma-Aldrich
Buchwald-Hartwig Amination in a Box
Sigma-Aldrich
Olefin Metathesis in a Box
Sigma-Aldrich
Negishi Coupling in a Box

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