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

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• 作者：Bruce H. Lipshutz ; Subir Ghorai ; Alexander R. Abela ; Ralph Moser ; Takashi Nishikata ; Christophe Duplais ; Arkady Krasovskiy ; Ricky D. Gaston ; Robert C. Gadwood
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：June 3, 2011
• 年：2011
• 卷：76
• 期：11
• 页码：4379-4391
• 全文大小：1220K
• 年卷期：v.76,no.11(June 3, 2011)
• ISSN：1520-6904

文摘

An environmentally benign surfactant (TPGS-750-M), a diester composed of racemic 伪-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 鈥渘ame鈥?reactions, including Heck, Suzuki鈭扢iyaura, Sonogashira, and Negishi-like couplings, have been studied using this technology, as have aminations, C鈭扝 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.