Organic & Biomolecular Chemistry 2008-11-21

A strategy for isotope containment during radiosynthesis--devolatilisation of bromobenzene by fluorous-tagging-Ir-catalysed borylation en route to the 4-phenylpiperidine pharmacophore.

Alan C Spivey, Laetitia J Martin, Chih-Chung Tseng, George J Ellames, Andrew D Kohler

Index: Org. Biomol. Chem. 6 , 4093-4095, (2008)

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Abstract

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.