Practical synthesis of 13C‐labeled conjugates by [13C]CO‐carbonylation of supported arylbipyridylpalladium complexes and alkyne–azide cycloadditions. (20th May 2020)

• Record Type: Journal Article
• Authors: Tabey, Alexis; Christine, Thifanie; Fouquet, Eric; Hermange, Philippe
• Is Part Of: Applied organometallic chemistry. Volume 34:Number 9(2020)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2020-05-20
• Subjects: arylbipyridylpalladium complexes -- carbonylation reactions -- positron emission tomography -- reactions on solid support; Organometallic chemistry -- Periodicals; Organometallic compounds -- Periodicals; 547.05
• DOI: 10.1002/aoc.5779
• Languages: English
• ISSNs: 0268-2605

Abstract

Abstract : A short procedure for the preparation of stable arylbipyridylpalladium complexes linked to a polystyrene resin is described. Starting from an o ‐iodobenzylalcohol with a pendant azido group, the corresponding supported complex was carbonylated with [ 13 C]CO to produce the desired 13 C‐labeled lactone tag with a satisfactory yield of 50%. This 13 C‐synthon was obtained with excellent purity after a simple filtration on sintered glass, and further conjugation using CuAAC and SPAAC reactions was performed with model substrates. Abstract : A new supported arylbipyridylpalladium complex bearing a pendant azido group was designed, and its carbonylation with substoichiometric amounts of [ 13 C]CO gave the corresponding 13 C‐labeled lactone tag with excellent purity after simple filtration. Its conjugation abilities were demonstrated by performing CuAAC and SPAAC reactions with model substrates.