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TPGS-750-M: A Second-Generation Amphiphile for Metal-Catalyzed Cross-Couplings in Water at Room Temperature

2011; American Chemical Society; Volume: 76; Issue: 11 Linguagem: Inglês

10.1021/jo101974u

1520-6904

Bruce H. Lipshutz, Subir Ghorai, Alexander R. Abela, Ralph Moser, Takashi Nishikata, Christophe Duplais, Arkady Krasovskiy, R.D. Gaston, Robert C. Gadwood,

Catalytic Cross-Coupling Reactions

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.