Manipulating Micellar Environments for Enhancing Transition Metal-Catalyzed Cross-Couplings in Water at Room Temperature

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• 作者：Bruce H. Lipshutz ; Subir Ghorai ; Wendy Wen Yi Leong ; Benjamin R. Taft ; Daniel V. Krogstad
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：June 17, 2011
• 年：2011
• 卷：76
• 期：12
• 页码：5061-5073
• 全文大小：1351K
• 年卷期：v.76,no.12(June 17, 2011)
• ISSN：1520-6904

文摘

The remarkable effects of added salts on the properties of aqueous micelles derived from the amphiphile PTS are described. Most notably, Heck reactions run in the presence of NaCl lead to couplings on aryl bromides in water at room temperature. Olefin cross- and ring-closing metathesis reactions run in the presence of small amounts of pH-lowering KHSO₄ are also accelerated, another phenomenon that does not apply to typical processes in organic media. These salt effects allow, in general, for synthetically valuable C鈥揅 bond-forming processes to be conducted under environmentally benign conditions. Recycling of the surfactant is also demonstrated.