Syntheses and characterization of polymer-supported organotrifluoroborates: applications in radioiodination reactions

Abstract

A novel strategy combining the advantages of polymer-supports and organotrifluoroborate chemistry for radiotracer preparation is reported.

Synthesis of PEG-supported organotrifluoroborates and their applications in palladium-catalyzed homo-coupling reactions

“…With the PEG-supported organotrifluoroborates (5) in hand, we investigated the homo-coupling reaction 9 . Although the transition metal-catalyzed, oxidative homo-coupling reactions of organoboron reagents are well known, 12 -19 most procedures require elevated temperatures.…”

“…1 The importance of these reports is that they validate the fact that boronated intermediates can "carry" a variety of pharmaceutically important functional groups late into reaction sequences. 5 The application of the Dowexsupported organotrifluoroborates in radioiodination 6 greatly simplified the purification procedure in the preparation of certain radiotracers (Scheme 1). 2 In radiolabeling chemistry, the removal of excess starting material is a significant issue.…”

Fluorous Analogue of Chloramine-T: Preparation, X-ray Structure Determination, and Use as an Oxidant for Radioiodination and s-Tetrazine Synthesis

“…These include polymer-supported [12][13][14][15][16] and fluorous labeling [17][18][19][20] methods that allow for expedited "HPLC-free" preparation of iodine-based radiopharmaceuticals. Although a great deal of emphasis has been placed on creating new labeling constructs, the nature of the oxidants used for iodination reactions has remained unchanged for some time.…”

Mild, Pd-catalyzed stannylation of radioiodination targets

“…12 Indirect methods include halodeboronation and halodestannylation. 13–16 In general, for radiolabeling of complex, bioactive molecules halodestannylation is preferred, partly owing to the facile separation of the radiohalogenated product and the metalated precursor. 17–19 …”