Maity Pradip K, Faisal Saqib, Rolfe Alan, Stoianova Diana, Hanson Paul R
Department of Chemistry, University of Kansas , 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, United States.
The University of Kansas Center for Chemical Methodologies and Library Development (KU-CMLD) , 2034-Becker Drive, Delbert M. Shankel Structural Biology Center, Lawrence, Kansas 66047, United States.
J Org Chem. 2015 Oct 16;80(20):9942-50. doi: 10.1021/acs.joc.5b01456. Epub 2015 Oct 2.
The syntheses of silica-supported oligomeric benzyl phosphates (Si-OBP(n)) and triazole phosphates (Si-OTP(n)) using ring-opening metathesis polymerization (ROMP) for use as efficient alkylating reagents is reported. Ease of synthesis and grafting onto the surface of norbornenyl-tagged (Nb-tagged) silica particles has been demonstrated for benzyl phosphate and triazole phosphate monomers. It is shown that these silica polymer hybrid reagents, Si-OBP(n) and Si-OTP(n), can be used to carry out alkylation reactions with an array of different nucleophiles to afford the corresponding benzylated and (triazolyl)methylated products in good yield and high purity.
报道了使用开环易位聚合(ROMP)合成二氧化硅负载的低聚苄基磷酸酯(Si-OBP(n))和三唑基磷酸酯(Si-OTP(n)),用作高效烷基化试剂。苄基磷酸酯和三唑基磷酸酯单体已证明易于合成并接枝到降冰片烯基标记(Nb标记)的二氧化硅颗粒表面。结果表明,这些二氧化硅聚合物杂化试剂Si-OBP(n)和Si-OTP(n)可用于与一系列不同亲核试剂进行烷基化反应,以高收率和高纯度得到相应的苄基化和(三唑基)甲基化产物。