Issue 30, 2021

Synthesis and [*C]CO-labelling of (C,N) gem-dimethylbenzylamine–palladium complexes for potential applications in positron emission tomography

Abstract

Various aryl–palladium complexes were synthesised from gem-dimethylbenzylamine derivatives by C–H activation under extremely mild conditions. Interestingly, these highly stable structures reacted with [13C]carbon monoxide to produce the desired labelled lactams in 29% to 51% yields over the C–H activation/carbonylation steps. As representative examples, a non-natural amino acid and an estradiol-based conjugate were prepared and labelled in model experiments with [13C]CO in homogeneous or heterogeneous conditions. Especially, the latter was radiolabelled with [11C]CO using a convenient procedure from the resin-supported palladium complex precursor. Thus, these results strongly suggest that cyclometallated palladium complexes obtained from gem-dimethylbenzylamine moieties are promising precursors for the practical synthesis of new [11C]tracers for Positron Emission Tomography.

Graphical abstract: Synthesis and [*C]CO-labelling of (C,N) gem-dimethylbenzylamine–palladium complexes for potential applications in positron emission tomography

Supplementary files

Article information

Article type
Paper
Submitted
19 May 2021
Accepted
29 Jun 2021
First published
20 Jul 2021

Dalton Trans., 2021,50, 10608-10614

Synthesis and [*C]CO-labelling of (C,N) gem-dimethylbenzylamine–palladium complexes for potential applications in positron emission tomography

M. Cormier, A. Tabey, T. Christine, H. Audrain, E. Fouquet and P. Hermange, Dalton Trans., 2021, 50, 10608 DOI: 10.1039/D1DT01633D

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