Skip to main content
Log in

Understanding the observed decreasing specific activity value in the series: aryl iodide, aryl bromide, aryl chloride during palladium catalyzed tritium dehalogenations

  • Published:
Journal of Radioanalytical and Nuclear Chemistry Aims and scope Submit manuscript

Abstract

The factors involved in the commonly observed decreasing specific activity value for the series aromatic iodide, aromatic bromide and aromatic chloride during palladium catalyzed tritium dehalogenations are explored.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Fig. 1

Similar content being viewed by others

References

  1. Lockley WJS, McEwen A, Cooke R (2012) Tritium: a coming of age for drug discovery and development ADME studies. J Label Compd Radiopharm 55:235–257

    Article  CAS  Google Scholar 

  2. Voges R, Heys JR, Moenius T (2009) Preparation of compounds labeled with tritium and carbon-14. Wiley, Chichester

    Book  Google Scholar 

  3. Saljoughian M (2002) Synthetic tritium labeling: reagents and methodologies. Synthesis 13:1781–1801

    Article  Google Scholar 

  4. Filer CN, Ahern DG (1989) The synthesis of glycine receptor radioligands [21, 22–3H] dihydrostrychnine and [2-3H] strychnine at high specific activity. J Label Compd Radiopharm 27:309–318

    Article  CAS  Google Scholar 

  5. Evans EA (1974) Tritium and its compounds. Wiley, New York

    Google Scholar 

  6. Wilkinson DJ, Hickey MJ, Kingston LP, Mather AN (2004) Tritio-dehalogenation: new variants on an old theme. Synthesis and applications of isotopically labelled compounds, vol 8. Wiley, pp 47–50

  7. Lockley WJS, Jones JR, Wilkinson DJ (2007) Investigations of isotope scrambling during the deuterodechlorination of ortho-chloroacetanilide. J Label Compd Radiopharm 50:505–506

    Article  CAS  Google Scholar 

  8. Lockley WJS, Wilkinson DJ, Jones JR (2006) Investigations of isotope scrambling during the deuterodechlorination of ortho-chloroacetanilide. J Label Compd Radiopharm 49:403–404

    Google Scholar 

  9. Janssen CGM, Verluyten WLM, Vliegen M (2006) Pd/C catalysed hydrogenolytic H/T exchange in solvents. Effects on solvents and product in a bromine-tritium exchange reaction. J Label Compd Radiopharm 49:219–222

    Google Scholar 

  10. Oehlke J, Bienert M, Niedrich H, Zopfl H-J, Franke P (1986) Catalytic dehalogenation of N-acetyl-L-4-chloro- and N-acetyl-L-4-iodophenylalanine amide in the presence of deuterium. J Label Compd Radiopharm 23:935–946

    Article  CAS  Google Scholar 

  11. Urbano FJ, Marinas JM (2001) Hydrogenolyis of organohalogen compounds over palladium supported catalysts. J Mol Catal A Chem 173:329–345

    Article  CAS  Google Scholar 

  12. Zhang Y, Liao S, Xu Y (1994) Highly active polymer anchored palladium catalyst for the hydrodehalogenation of organic halides under mild conditions. Tet Lett 35:4599–4602

    Article  CAS  Google Scholar 

  13. Aramendia MA, Borau V, Garcia IM, Jimenez C, Marinas JM, Marinas A, Urbano FJ (2000) Hydrodehalogenation of aryl halides by hydrogen gas and hydrogen transfer in the presence of palladium catalysts. Stud Surf Sci Catal 130:2003–2008

    Article  Google Scholar 

  14. Ukisu Y, Miyadera T (1997) Hydrogen-transfer hydrodehalogenation of aromatic halides with alcohols in the presence of noble metal catalysts. J Mol Catal A Chem 125:135–142

    Article  CAS  Google Scholar 

  15. Wiener H, Blum J, Sasson Y (1991) Transfer hydrogenolysis of aryl halides and other hydrogen acceptors by formate salts in the presence of Pd/C catalyst. J Org Chem 56:6145–6148

    Article  CAS  Google Scholar 

  16. Faucher N, Ambroise Y, Cintrat J-C, Doris E, Pillon F, Rousseau B (2002) Highly chemoselective hydrogenolysis of iodoarenes. J Org Chem 67:932–934

    Article  CAS  Google Scholar 

  17. Marques CA, Selva M, Tundo P (1993) Facile hydrodehalogenation with hydrogen and Pd/C catalyst under multiphase conditions. J Org Chem 58:5256–5260

    Article  CAS  Google Scholar 

  18. Ambroise Y, Mioskowski C, Djega-Mariadassou G, Rousseau B (2000) Consequences of affinity in heterogeneous catalytic reactions: highly chemoselective hydrogenolysis of iodoarenes. J Org Chem 65:7183–7186

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We would like to acknowledge the contribution of Dr. Puliyer Srinivasan of PerkinElmer Life Sciences & Technology Inc. for obtaining the tritium NMR spectrum.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Crist N. Filer.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Filer, C.N. Understanding the observed decreasing specific activity value in the series: aryl iodide, aryl bromide, aryl chloride during palladium catalyzed tritium dehalogenations. J Radioanal Nucl Chem 297, 79–82 (2013). https://doi.org/10.1007/s10967-012-2309-6

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10967-012-2309-6

Keywords

Navigation