Synthesis and [*C]CO-labelling of (C, N) gem-dimethylbenzylamine–palladium complexes for potential applications in positron emission tomography. Issue 30 (20th July 2021)

• Record Type: Journal Article
• Authors: Cormier, Morgan; Tabey, Alexis; Christine, Thifanie; Audrain, Hélène; Fouquet, Eric; Hermange, Philippe
• Is Part Of: Dalton transactions. Volume 50:Issue 30(2021)
• Page Start: 10608
• Page End: 10614
• Publication Date: 2021-07-20
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/d1dt01633d
• Languages: English
• ISSNs: 1477-9226

Abstract

Abstract : 13 C- and 11 C-labelled conjugates were produced in one step upon carbonylation of homogeneous or heterogeneous arylpalladium complexes synthesised by mild C–H activation of gem -dimethylbenzylamine derivatives. 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 [ 13 C]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 [ 13 C]CO in homogeneous or heterogeneous conditions. Especially, the latter was radiolabelled with [ 11 C]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 [ 11 C]tracers for Positron Emission Tomography.