A strategy for isotope containment during radiosynthesis - Devolatilisation of bromobenzene by fluorous-tagging-Ir-catalysed borylation en route to the 4-phenylpiperidine pharmacophore

Organic and Biomolecular Chemistry

Volumn 6, Issue 22, 2008, Pages 4093-4095

  Spivey, Alan C ^a   Martin, Laetitia J ^a   Tseng, Chih Chung ^a   Ellames, George J ^b   Kohler, Andrew D ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b Sanofi Synthelabo Inc   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT; COBALT COMPOUNDS; PALLADIUM;

BORYLATION; BROMOBENZENE; DEVOLATILISATION; EN ROUTES; FLUOROUS; MATERIAL LOSSES; PHARMACOPHORE; RADIOSYNTHESIS; STARTING MATERIALS;

IRIDIUM;

4 PHENYLPIPERIDINE; 4-PHENYLPIPERIDINE; BORON; BROMOBENZENE; IRIDIUM; ISOTOPE; PIPERIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; RADIOCHEMISTRY; VOLATILIZATION;

BORON; BROMOBENZENES; CATALYSIS; IRIDIUM; ISOTOPES; PIPERIDINES; RADIOCHEMISTRY; VOLATILIZATION;

EID: 55549142532     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b816217b     Document Type: Article

References (30)

1. S. Scheindlin Mol. Interventions 2004 4 188 191
2. W. Zhang D. P. Curran Tetrahedron 2006 62 11837 11865
3. D. G. Hall, Boronic Acids, ed., D. G. Hall, Wiley-VCH, Weinheim, 2005
4. M. Genov A. Almorín P. Espinet Chem.-Eur. J. 2006 12 9346 9352
5. D. A. Horton G. T. Bourne M. L. Smythe Chem. Rev. 2003 103 893 930
6. X. Emonds-Alt, P. Soubrie and R. Steinberg, WO 2000, 064423 (2 Nov 2000)
7. A. Iwashita N. Tojo S. Matsuura S. Yamazaki K. Kamijo J. Ishida H. Yamamoto K. Hattori N. Matsuoka S. Mutoh J. Pharmacol. Exp. Ther. 2004 310 425 436
8. D. J. Turner R. Anémian P. R. Mackie D. C. Cupertino S. G. Yeates M. L. Turner A. C. Spivey Org. Biomol. Chem. 2007 5 1752 1763
9. G. A. M. Giardina M. Grugni R. Rigolio M. Vassallo K. Erhard C. Farina Bioorg. Med. Chem. Lett. 1996 6 2307 2310
10. E. J. Corey G. A. Reichard S. Sarshar Bioorg. Med. Chem. Lett. 1993 3 2635 2636
11. H. Chen S. Schlecht T. C. Semple J. F. Hartwig Science 2000 287 1995 1997
12. M. K. Tse J.-Y. Cho M. R. Smith, III Org. Lett. 2001 3 2831 2833
13. H. Chen J. F. Hartwig Angew. Chem., Int. Ed. 1999 38 3391 3393
14. T. Ishiyama J. Takagi J. F. Hartwig N. Miyaura Angew. Chem., Int. Ed. 2002 41 3056 3058
15. J. Takagi K. Sato J. F. Hartwig T. Ishiyama N. Miyaura Tetrahedron Lett. 2002 43 5649 5651
16. A. C. Spivey C. M. Diaper H. Adams A. J. Rudge J. Org. Chem. 2000 65 5253 5263
17. J. L. Herde J. C. Lambert C. V. Senoff M. A. Cushing Inorg. Synth. 1974 15 18 20
18. R. Uson L. A. Oro J. A. Cabeza H. E. Bryndza P. Stepro Inorg. Synth. 1985 23 126 130
19. G. A. Chotana M. A. Rak M. R. Smith, III J. Am. Chem. Soc. 2005 127 10539 10544
20. H. Hata H. Shinokubo A. Osuka J. Am. Chem. Soc. 2005 127 8264 8265
21. J. Uenishi J.-M. Beau R. W. Amstrong Y. Kishi J. Am. Chem. Soc. 1987 109 4756 4758
22. S. Talluri A. Sudalai Org. Lett. 2005 7 855 857
23. J. Waser E. M. Carreira J. Am. Chem. Soc. 2004 126 5676 5677
24. J. Waser E. M. Carreira Angew. Chem., Int. Ed. 2004 43 4099 4102
25. J. Waser B. Gaspar H. Nambu E. M. Carreira J. Am. Chem. Soc. 2006 128 11693 11712
26. G. A. M. Giardina M. Grugni R. Rigolio M. Vassallo K. Erhard C. Farina Bioorg. Med. Chem. Lett. 1996 6 2307 2310
27. S. Inoki K. Kato S. Isayama T. Mukaiyama Chem. Lett. 1990 1869 1872
28. P. Magnus M. R. Fielding Tetrahedron Lett. 2001 42 6633 6636
29. P. Magnus A. H. Payne M. J. Waring D. A. Scott V. Lynch Tetrahedron Lett. 2000 41 9725 9730
30. H. G. Chen O. P. Goel J. Knobelsdorf Tetrahedron Lett. 1996 37 8129 8132