title: Ring-opening metathesis polymerization-based recyclable magnetic acylation reagents.
abstract: An operationally simple method for the acylation of amines utilizing carbon-coated metal nanoparticles as recyclable supports is reported. Highly magnetic carbon-coated cobalt (Co/C) and iron (Fe/C) nanobeads were functionalized with a norbornene tag (Nb-tag) through a "click" reaction followed by surface activation employing Grubbs-II catalyst and subsequent grafting of acylated N-hydroxysuccinimide ROMPgels (ROMP=ring-opening metathesis polymerization). The high loading (up to 2.6 mmolg(-1) ) hybrid material was applied in the acylation of various primary and secondary amines. The products were isolated in high yields (86-99%) and excellent purities (all >95 % by NMR spectroscopy) after rapid magnetic decantation and simple evaporation of the solvents. The spent resins were successfully re-acylated by acid chlorides, anhydrides, and carboxylic acids and reused for up to five consecutive cycles without considerable loss of activity.
authors: Institute for Organic Chemistry, University of Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany.
authors: Quirin M
authors: QM
authors: Kainz
authors: Roland
authors: R
authors: Linhardt
authors: Pradip K
authors: PK
authors: Maity
authors: Paul R
authors: PR
authors: Hanson
authors: Oliver
authors: O
authors: Reiser
mesh_terms: D000215:Acylation; D002244:Carbon / Q000737:chemistry; D003035:Cobalt / Q000737:chemistry*; D007501:Iron / Q000737:chemistry*; D060328:Magnetic Phenomena; D053768:Metal Nanoparticles / Q000737:chemistry*; D009636:Norbornanes / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D058105:Polymerization; D059027:Recycling; D013388:Succinimides / Q000737:chemistry*
chemical_list: D009636:Norbornanes; D009942:Organometallic Compounds; D013388:Succinimides; C524958:bis(trichlorohexylphosphine)benzylideneruthenium; D003035:Cobalt; D002244:Carbon; D007501:Iron; C001426:N-hydroxysuccinimide