Development of a new ultraporous polymer as support in organic synthesis.
This paper describes the preparation and post-functionalisation of a new polymeric support based on emulsion-derived foams and called polyHIPEs. The remaining pendant vinylic bonds are easily functionalised by a free radical mechanism. The large pores and channels of this material allow an easy access of the reagent in solution toward the grafted species. PolyHIPE-supported thiol, in the presence of an excess of triethylsilane, showed a good activity and selectivity toward reductive cyclisation of 6-bromohex-1-ene and 1-allyloxy-2-bromobenzene.
Deleuze
Hervé
H
Laboratoire de Chimie Organique et Organométallique UMR 5802-CNRS, Université Bordeaux I 33405, Talence, France. h.deleuze@lcoo.u-bordeaux.fr
Maillard
Bernard
B
Mondain-Monval
Olivier
O
D002625:Chemistry, Organic / Q000379:methods*; D004655:Emulsions / Q000138:chemical synthesis; D005609:Free Radicals / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis*; D008855:Microscopy, Electron, Scanning; D010084:Oxidation-Reduction; D011108:Polymers / Q000737:chemistry*; D011137:Polystyrenes / Q000737:chemistry; D016062:Porosity; D012821:Silanes / Q000737:chemistry; D012995:Solubility; D013438:Sulfhydryl Compounds / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry
D004655:Emulsions; D005609:Free Radicals; D006842:Hydrocarbons, Brominated; D006844:Hydrocarbons, Cyclic; D011108:Polymers; D011137:Polystyrenes; D012821:Silanes; D013438:Sulfhydryl Compounds; D014753:Vinyl Compounds