“Nok”: A Phytosterol-Based Amphiphile Enabling Transition-Metal-Catalyzed Couplings in Water at Room Temperature

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• 作者：Piyatida Klumphu ; Bruce H. Lipshutz
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：February 7, 2014
• 年：2014
• 卷：79
• 期：3
• 页码：888-900
• 全文大小：770K
• ISSN：1520-6904

文摘

The third-generation designer amphiphile/surfactant, 鈥淣ok鈥?(i.e., SPGS-550-M; 尾-sitosterol methoxypolyethyleneglycol succinate), soon to be commercially available from Aldrich, can be prepared in two steps using an abundant plant feedstock and 尾-sitosterol, together with succinic anhydride and PEG-550-M. Upon dissolution in water, it forms nanomicelles that serve as nanoreactors, which can be characterized by both cryo-TEM and dynamic light scattering analyses. Several transition-metal-catalyzed reactions have been run under micellar conditions to evaluate this surfactant relative to results obtained in nanoparticles composed of TPGS-750-M (i.e., a second-generation surfactant). It is shown that Nok usually affords yields that are, in general, as good or better than those typically obtained with TPGS-750-M, and yet is far less costly.