Olefin metathesis in homogenous aqueous media catalyzed by conventional ruthenium catalysts

Olefin metathesis in homogenous aqueous media catalyzed by conventional ruthenium catalysts
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DOI:
10.1021/ol7022505
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发表时间:
2007-11-08
期刊:
影响因子:
5.2
通讯作者:
Raines, Ronald T.
Raines, Ronald T.
中科院分区:
化学1区
文献类型:
--
作者:
Binder, Joseph B.;Blank, Jacqueline J.;Raines, Ronald T.

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在水溶剂中的烯烃复分解被寻求用于绿色化学和化学生物学的亲水性底物,如蛋白质和多糖。然而,大多数在水中的复分解实验都是利用外来配合物。我们已经研究了常规催化剂在均相水/有机混合物中的性能,发现第二代Hoveyda-Grubbs催化剂在含水二甲氧基乙烷和含水丙酮中具有非凡的效率。在这些溶剂体系中,各种底物的闭环和交叉复分解实现了高(71-95%)转化率。
Olefin metathesis in aqueous solvents is sought for applications in green chemistry and with the hydrophilic substrates of chemical biology, such as proteins and polysaccharides. Most demonstrations of metathesis in water, however, utilize exotic complexes. We have examined the performance of conventional catalysts in homogeneous water/organic mixtures, finding that the second-generation Hoveyda-Grubbs catalyst has extraordinary efficiency in aqueous dimethoxyethane and aqueous acetone. High (71-95%) conversions are achieved for ring-closing and cross metathesis of a variety of substrates in these solvent systems.