Iridium-catalysed labelling of anilines, benzylamines and nitrogen heterocycles using deuterium gas and cycloocta-1,5-dienyliridium(I) 1,1,1,5,5,5-hexafluoropentane-2,4-dionate

Tetrahedron Letters

Volumn 44, Issue 20, 2003, Pages 3959-3961

  Hickey, Michael J ^a   Jones, John R ^b   Kingston, Lee P ^a   Lockley, William J S ^b   Mather, Andrew N ^a   McAuley, Barry M ^a   Wilkinson, David J ^a  

^a ASTRAZENECA   (United Kingdom)

^b UNIVERSITY OF SURREY   (United Kingdom)

Author keywords

Acetylacetonate; Anilines; Benzylamines; CH activation; Cycloocta 1,5 diene; Cycloocta 1,5 dienyliridium(I) 1,1,1,5,5,5 hexafluoropentane 2,4 dionate; Deuteration; Isotope exchange; Ortho labelling

Indexed keywords

ANILINE DERIVATIVE; BENZYLAMINE DERIVATIVE; CYCLOOCTA 1,5 DIENYLIRIDIUM 1,1,1,5,5,5 HEXAFLUOROPENTANE 2,4 DIONATE; DEUTERIUM; IRIDIUM COMPLEX; ISOTOPE; N,N DIMETHYLACETAMIDE; N,N DIMETHYLFORMAMIDE; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; DRUG INDUSTRY;

EID: 0242417480     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00750-0     Document Type: Article

References (23)

1. Lockley W.J.S. Tetrahedron Lett. 23:1982;3819-3822.
2. Lockley W.J.S. J. Lab. Comp. Radiopharm. 21:1984;45-57.
3. Lockley W.J.S. J. Lab. Comp. Radiopharm. 22:1985;623-630.
4. Lockley W.J.S. J. Chem. Res. (S). 1985;178-179. and J. Chem. Res (M) 1985, 1976-1986 Wilkinson, D. J. M. Phil. Thesis, University of Surrey, 1995.
5. Lockley W.J.S. J. Chem. Res. (S). 1985;178-179. and J. Chem. Res (M) 1985, 1976-1986 Wilkinson, D. J. M. Phil. Thesis, University of Surrey, 1995.
6. Hesk D., Jones J.R., Lockley W.J.S. J. Pharm. Sci. 80:1991;887-890.
7. Oohashi K., Seki T. J. Radioan. Nucl. Chem. Lett. 187:1994;303-311.
8. Heys J.R. J. Chem. Soc., Chem. Commun. 1992;680.
9. Heys J.R., Shu A.Y.L., Senderoff S.G., Phillips N.M. J. Lab. Comp. Radiopharm. 33:1993;431-438.
10. Shu A.Y.L., Heys J.R. J. Lab. Comp. Radiopharm. 34:1994;587.
11. Ellames G.J., Gibson J.S., Herbert J.M., Kerr W.J., McNeil A.H. Tetrahedron Lett. 42:2001;6413-6416.
12. Ellames G.J., Gibson J.S., Herbert J.M., McNeil A.H. Tetrahedron. 57:2001;9487-9497 Salter, R.; Chappelle, M. R.; Morgan, A.; Moenius, T.; Ackerman, P.; Studer, M.; Spindler, F. Synth. Appl. Isotop. Lab. Comp. Proc. Int. Symp.; Pleiss, U.; Voges, R., Eds.; John Wiley & Sons Ltd, 2001; Vol. 7, pp. 63-67.
13. Chen W., Garnes K.T., Levinson S.H., Saunders D., Senderoff S.G., Shu A.Y.L., Villani A.J., Heys J.R. J. Lab. Comp. Radiopharm. 39:1997;291-298.
14. Shu A.Y.L., Saunders D., Levinson S., Landvatter S.W., Mahoney A., Senderoff S.G., Mack J.F., Heys J.R. J. Lab. Comp. Radiopharm. 34:1999;797-807.
15. Hesk D., Das P.R., Evans B. J. Lab. Comp. Radiopharm. 36:1995;497-502 Valsborg, J. S.; Sorensen, L.; Foged, C. Synth. Appl. Isot. Lab. Comp. Proc. Int. Symp.; Pleiss, U.; Voges, R., Eds.; John Wiley & Sons, 2001; Vol. 7, pp. 72-75.
16. Crabtree R.H. Acc. Chem. Res. 12:1979;331-337.
17. Crabtree R.H., Davis M.W. J. Org. Chem. 51:1986;2655-2661.
18. Crabtree R.H., Morehouse S.M. Inorg. Synth. 24:1986;173-176.
19. Kingston L.P., Lockley W.J.S., Mather A.N., Spink E., Thompson S.P., Wilkinson D.J. Tetrahedron Lett. 41:2000;2705-2708.
20. 3) 31.1, 62.6, 93.1, 118.5 (quartet), 174.3 (quartet) ppm. MS (EI mode) m/z 508/506 a.m.u. Found C, 30.55%; H, 2.91%, req. C, 30.67%; H, 2.95%.
21. A typical deuteration protocol is as follows: The substrate (0.04 mmol) and catalyst (0.01 mmol) were dissolved in DMF or DMA (250 μl) and stirred under deuterium gas for 4 h at room temperature. The labelled substrate was then isolated by a suitable solvent extraction procedure, e.g. for anilines and benzylamines, an ether/hydrochloric acid partition, basification with NaOH solution, extraction into ether and removal of the solvent under a stream of dry nitrogen.
22. Crabtree R.H., Demou P.C., Eden D., Mihelcic J.M., Parnell C.M., Quirk J.M., Morris G.E. J. Am. Chem. Soc. 104:1982;6994-7001.
23. Anton D.R., Crabtree R.H. Organometallics. 2:1983;855-859.