Binder Joseph B, Blank Jacqueline J, Raines Ronald T
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706-1322, USA.
Org Lett. 2007 Nov 8;9(23):4885-8. doi: 10.1021/ol7022505. Epub 2007 Oct 19.
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.
人们寻求在水性溶剂中进行烯烃复分解反应,以应用于绿色化学以及化学生物学的亲水性底物(如蛋白质和多糖)。然而,大多数在水中进行复分解反应的实例都使用了特殊的配合物。我们研究了传统催化剂在均相水/有机混合物中的性能,发现第二代霍维达-格鲁布斯催化剂在二甲基乙氧基水溶液和丙酮水溶液中具有非凡的效率。在这些溶剂体系中,各种底物的闭环复分解反应和交叉复分解反应都能实现高转化率(71-95%)。