A strategy for isotope containment during radiosynthesis--devolatilisation of bromobenzene by fluorous-tagging-Ir-catalysed borylation en route to the 4-phenylpiperidine pharmacophore.
Syntheses of two 4-phenylpiperidines from bromobenzene have been developed involving anchoring to a fluorous-tag, Ir-catalysed borylation, Pd- and Co-catalysed elaboration then traceless cleavage. Although performed using 'cold' (i.e. unlabelled) bromobenzene as the starting material, these routes have been designed to minimise material loss via volatile intermediates and expedite purification during radiosynthesis from 'hot' (i.e. [(14)C] labelled) bromobenzene.
Spivey
Alan C
AC
Department of Chemistry, South Kensington Campus, Imperial College, London, SW7 2AZ, UK. a.c.spivey@imperial.ac.uk
Martin
Laetitia J
LJ
Tseng
Chih-Chung
CC
Ellames
George J
GJ
Kohler
Andrew D
AD
D001895:Boron / Q000737:chemistry*; D001969:Bromobenzenes / Q000737:chemistry*; D002384:Catalysis; D007495:Iridium / Q000737:chemistry*; D007554:Isotopes; D010880:Piperidines / Q000737:chemistry*; D011854:Radiochemistry; D014835:Volatilization
D001969:Bromobenzenes; D007554:Isotopes; D010880:Piperidines; D007495:Iridium; C048151:4-phenylpiperidine; C032036:bromobenzene; D001895:Boron