A convenient method to remove ruthenium byproducts from olefin metathesis reactions using polymer-bound triphenylphosphine oxide (TPPO).
Ruthenium byproducts from ring-closing metathesis reactions can be removed by refluxing the crude reaction mixture with resin-bound triphenylphosphine oxide (TPPO) in toluene or by stirring with dimethyl sulfoxide (DMSO) and silica gel at room temperature. Residual levels of ruthenium can be achieved that are as low as 0.04 microg per 5 mg of product when a combination of TPPO, DMSO, and silica gel is used. The polymer-bound TPPO retained its efficiency after being recycled six times.
Haack
KyoungLang
K
Department of Medicinal Chemistry, Center for Cancer Experimental Therapeutics, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582, USA.
Ahn
Yu Mi
YM
Georg
Gunda I
GI
D000475:Alkenes / Q000737:chemistry*; D004121:Dimethyl Sulfoxide; D008956:Models, Chemical; D009943:Organophosphorus Compounds / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry* / Q000302:isolation & purification*; D012822:Silicon Dioxide
D000475:Alkenes; D009943:Organophosphorus Compounds; D011108:Polymers; D012822:Silicon Dioxide; D012428:Ruthenium; D004121:Dimethyl Sulfoxide; C063888:triphenylphosphine oxide