Supported Synthesis of Halogenated
Organic Compounds

Sophie Boldon; Ida S. R. Stenhagen; Jane E. Moore; Sajinder K. Luthra; Véronique Gouverneur

doi:10.1055/s-0031-1289590

REVIEW

Supported Synthesis of Halogenated Organic Compounds

Sophie Boldon^a, Ida S. R. Stenhagen^a, Jane E. Moore^b, Sajinder K. Luthra^c, Véronique Gouverneur*^a
^a Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK
Fax: +44(1865)275644; e-Mail: veronique.gouverneur@chem.ox.ac.uk;
^b AstraZeneca UK, Alderley Park, Cheshire, SK10 4TG, UK
^c GE Healthcare, The Grove Centre, White Lion Road, Amersham, HP7 9LL, UK

Abstract

Alle Artikel dieser Rubrik

Abstract

Halogenated organic compounds are highly sought after in a wide variety of fields, for example synthetic and medicinal chemistry as well as materials science. The supported synthesis of organohalogens has been extensively developed in the field of imaging where rapid purification of radiotracers containing isotopes with short half-lives is of great importance. Electrophilic and nucleophilic halogenation occurs upon cleavage from the support and the desired labeled product is readily separated from contaminants. This review provides a discussion as to how supported synthetic routes have facilitated the preparation of halogenated compounds.

1 Introduction

2 Halogenation of Supported Precursors

2.1 Fluorination

2.2 Chlorination

2.3 Bromination

2.4 Iodination

3 Conclusion

Key words

halogenation - solid support - fluorous - radiochemistry - detagging

Volltext

Referenzen

References

For reviews on solid-phase synthesis see:

1a Guillier F. Orain D. Bradley M. Chem. Rev. 2000, 100: 2091

1b Bräse S. Dahmen S. Chem. Eur. J. 2000, 6: 1899

1c Gil C. Bräse S. Curr. Opin. Chem. Biol. 2004, 8: 230

1d Bräse S. Acc. Chem. Res. 2004, 37: 805

1e Scott PJH. Steel PG. Eur. J. Org. Chem. 2006, 2251

1f Merrifield RB. J. Am. Chem. Soc. 1963, 85: 2149

2a Gribble GW. Acc. Chem. Res. 1998, 31: 141

2b Gribble GW. J. Chem. Educ. 2004, 81: 1441

2c O’Hagan D. Harper DB. J. Fluorine Chem. 1999, 100: 127

2d Gribble GW. Naturally Occurring Organohalogen Compounds - A Comprehensive Update Springer-Verlag; Vienna: 2010.

For reviews on fluorine in medicinal chemistry see:

3a Böhm H.-J. Banner D. Bendels S. Kansy M. Kuhn B. Müller K. Obst-Sander U. Stahl M. ChemBioChem 2004, 5: 637

3b Müller K. Faeh C. Diederich F. Science 2007, 317: 1881

3c Purser S. Moore PR. Swallow S. Gouverneur V. Chem. Soc. Rev. 2008, 37: 320

3d Hagmann WK. J. Med. Chem. 2008, 51: 4359

4a Thomas G. Medicinal Chemistry: An Introduction Wiley; New York: 2000.

4b Metal-Catalyzed Cross-Coupling Reactions 2nd ed.: de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004.

4c Corbet J.-P. Mignani G. Chem. Rev. 2006, 106: 2651

4d Fairlamb I. Chem. Soc. Rev. 2007, 36: 1036

4e Amii H. Uneyama K. Chem. Rev. 2009, 109: 2119

For reviews on molecular imaging see:

5a Kugaya A. Fujita M. Innis RB. Ann. Nucl. Med. 2000, 14: 1

5b Schyler DJ. Ann. Acad. Med. Singapore 2004, 33: 146

5c Wester H.-J. Clin. Cancer Res. 2007, 13: 3470

5d Taki J. Matsunari I. Eur. J. Nucl. Med. Mol. Imaging 2007, 34: S34

5e Yamashina S. Yamazaki J. Eur. J. Nucl. Med. Mol. Imaging 2007, 34: S62

5f Ametamey SM. Honer M. Schubiger PA. Chem. Rev. 2008, 108: 1501

5g Holland GN. Bottomley PA. Hinshaw WS.
J. Magn. Reson. 1977, 28: 133

5h Janjic JM. Ahrens ET. WIREs Nanomed. Nanobio. 2009, 1: 492

6 Gladysz JA. Curran DP. Horvath IT. Handbook of Fluorous Chemistry Wiley-VCH; Weinheim: 2004.

For reviews on fluorous-phase synthesis see:

7a Zhang W. Tetrahedron 2003, 59: 4475

7b Zhang W. Chem. Rev. 2004, 104: 2531

7c Dandapani S. QSAR Comb. Sci. 2006, 25: 681

7d Zhang W. Curran DP. Tetrahedron 2006, 62: 11837

7e Zhang W. Cai C. Chem. Commun. 2008, 5686

7f Curran DP. Science 2008, 321: 1645

7g Zhang W. Chem. Rev. 2009, 109: 749

8a Pollack A. Roe DG. Pollack CM. Lu LFL. Thornback JR. J. Am. Chem. Soc. 1999, 121: 11593

8b Dunn-Default R. Pollak A. Fitzgerald J. Thornback JR. Ballinger JR. Nucl. Med. Biol. 2000, 27: 803

8c Maclean D. Zhu J. Chen M. Hale R. Satymurthy N. Barrio JR. J. Am. Chem. Soc. 2003, 125: 10168

8d Mundwiler S. Candreia L. Hafliger P. Ortner K. Alberto R. Bioconjugate Chem. 2004, 15: 195

For reviews of ^¹8F-radiochemistry see:

9a Schirrmacher R. Wängler C. Schirrmacher E. Mini-Rev. Org. Chem. 2007, 4: 317

9b Miller PW. Long NJ. Vilar R. Gee AD. Angew. Chem. Int. Ed. 2008, 47: 8998

10 Cai L. Lu S. Pike VW. Eur. J. Org. Chem. 2008, 2853

11a Beuthien-Baumann B. Hamacher K. Oberdorfer F. Steinbach J. Carbohydr. Res. 2000, 327: 107

11b Couturier O. Luxen A. Chatal J.-F. Vuillez J.-P. Rigo P. Hustinx R. Eur. J. Nucl. Med. Mol. Imaging 2004, 31: 1182

12 Tooronigan SA. Mulholland GK. Jewett DM. Bachelor MA. Kilbourn MR. Nucl. Med. Biol. 1990, 17: 273

13 Kuge Y. Nishijima K. Nagatsu K. Seki K. Ohkura K. Tanaka A. Sasaki M. Tsukamoto E. Tamaki N. Nucl. Med. Biol. 2002, 29: 275

14 Ohsaki K. Endo Y. Yamazaki S. Tomoi M. Iwata R. Appl. Radiat. Isot. 1998, 49: 373

15 Tang G. Wang M. Tang X. Luo L. Gan M. Nucl. Med. Biol. 2003, 30: 509

16 Tang G. Wang M. Tang X. Luo L. Gan M. Appl. Radiat. Isot. 2003, 58: 685

17 Olah GA. Li XY. Synlett 1990, 267

18 Sket B. Zupan M. Zupet P. Tetrahedron 1984, 40: 1603

19 Brown LJ. Bouvet DR. Champion S. Gibson AM. Hu Y. Jackson A. Khan I. Ma N. Millot N. Wadsworth H. Brown RCD. Angew. Chem. Int. Ed. 2007, 46: 941

20 Brown LJ. Ma N. Bouvet DR. Champion S. Gibson AM. Gibson AM. Hu Y. Jackson A. Khan I. Millot N. Topley AC. Wadsworth H. Wynn D. Brown RCD. Org. Biomol. Chem. 2009, 7: 564

21 Gibson AM, Brown LJ, and Brown CD. inventors; PCT Int. Appl. WO 056725 A1.

22 Luthra SK, Brady F, Wadsworth HJ, Gibson AM, and Glaser ME. inventors; PCT Int. Appl. WO 002157 A1.

23 Brady F, Luthra SK, and Gibson AM. inventors; PCT Int. Appl. WO 056399 A2.

24a Shah A. Pike VW. Widdowson DA. J. Chem. Soc. Perkin Trans. 1 1998, 2043

24b Ermert J. Hocke C. Ludwig T. Gail R. Coenen HH. J. Labelled Compd. Radiopharm. 2004, 47: 429

24c Zhang M.-R. Kumata K. Suzuki K. Tetrahedron Lett. 2007, 48: 8632

25a Chun J.-H. Lu S. Lee Y.-S. Pike VW. J. Org. Chem. 2010, 75: 3332

25b Brady F, Luthra SK, and Robins EG. inventors; PCT Int. Appl. WO 056400 A1.

26a Carroll L. Boldon S. Bejot R. Moore JE. Declerck J. Gouverneur V. Org. Biomol. Chem. 2010, 9: 136

26b Bejot R. Fowler T. Carroll L. Boldon S. Moore JE. Declerck J. Gouverneur V. Angew. Chem. Int. Ed. 2009, 48: 586

26c Bejot R, and Gouverneur V. inventors; PCT Int. Appl. WO 007363 A2.

27a Johnström PS. Stone-Elander S. Appl. Radiat. Isot. 1996, 47: 401

27b Füchtner F. Preusche S. Mäding P. Zessin J. Steinbach J. Nuklearmedizin 2008, 3: 116

28a Blom E. Karimi F. Långström B. J. Labelled Compd. Radiopharm. 2010, 53: 24

28b Långström B, and Blom E. inventors; PCT Int. Appl. WO 106442 A1.

29 Blom E. Karimi F. Långström B. J. Labelled Compd. Radiopharm. 2009, 52: 504

30 Långström B, and Kihlberg T. inventors; PCT Int Appl. WO 029633 A1.

31 Srinivasan A, Berndt M, Graham K, Friebe M, and Schmitt-Willich H. inventors; PCT Int. Appl. WO 000409 A2.

32a Långström B, and Farhad K. inventors; PCT Int. Appl. WO 073273.

32b Långstrom B, and Farhad K. inventors; PCT Int. Appl. US 0228060 A1.

33 Wiehn MS. Lindell SD. Bräse S. Angew. Chem. Int. Ed. 2008, 47: 8120

34 Wiehn MS. Lindell SD. Bräse S. J. Comb. Chem. 2009, 11: 960

35 Wiehn MS. Fürness D. Bräse S. J. Comb. Chem. 2009, 11: 982

36 Döbele M. Vanderheiden S. Jung N. Bräse S. Angew. Chem. Int. Ed. 2010, 49: 5986

37a Dollé F. Demphel S. Hinnen F. Fournier D. Vaufrey F. Crouzel C. J. Labelled Compd. Radiopharm. 1998, 41: 105

37b Forsback S. Eskola O. Haaparanta M. Bergman J. Solin O. Radiochimica Acta 2008, 96: 845

38 Kawai K. Channing MA. Kiesewetter DO. Eckelman WC. Nucl. Med. Biol. 1995, 22: 37

39 Szajek LP. Channing MA. Eckelman WC. Appl. Radiat. Isot. 1998, 49: 795

40 Luthra SK, Brady F, and Wadsworth HJ. inventors; PCT Int. Appl. WO 002489 A2.

41 Valliant JF. inventors; US 2004/0260073 A1.

42a Boldon SE. Moore JE. Gouverneur V. Chem. Commun. 2008, 3622

42b Thibaudeau S. Gouverneur V. Org. Lett. 2003, 5: 4891

42c Pacheco MC. Purser S. Gouverneur V. Chem. Rev. 2008, 108: 1943

42d Carroll L. McCullough S. Rees T. Claridge TDW. Gouverneur V. Org. Biomol. Chem. 2008, 6: 1731

42e Lam Y.-h. Bobbio C. Cooper IR. Gouverneur V. Angew. Chem. Int. Ed. 2007, 46: 5106

42f Purser S. Wilson C. Moore PR. Gouverneur V. Synlett 2007, 1166

42g Carroll L. Garcia L. Pacheco MC. Gouverneur V. Chem. Commun. 2006, 4113

42h Greedy B. Paris J.-M. Vidal T. Gouverneur V. Angew. Chem. Int. Ed. 2003, 42: 3291

42i Pacheco MC. Gouverneur V. Org. Lett. 2005, 7: 1267

42j Greedy B. Gouverneur V. Chem. Commun. 2001, 233

43 Pilot C. Dahmen S. Lauterwasser F. Bräse S. Tetrahedron Lett. 2001, 42: 9179

44 Spivey AC. Diaper CM. Rudge AJ. Chem. Commun. 1999, 835

45a Nicolaou KC. Pastor J. Barluenga S. Winssinger N. Chem. Commun. 1998, 1947

45b Sheng S.-R. Huang X. Org. Prep. Proced. Int. 2003, 35: 383

45c Sheng S.-R. Huang X. Tetrahedron Lett. 2001, 42: 9035

45d Dewry DH. Coe DM. Poon S. Med. Res. Rev. 1999, 19: 97

45e Nicolaou KC. Pfefferkorn JA. Cao GQ. Angew. Chem. Int. Ed. 2000, 39: 734

46a Zajc B. Zupan M. Tetrahedron 1989, 45: 7869

46b Zupan M. Šegatin N. Synth. Commun. 1994, 24: 2617

46c Ley SV. Baxendale IR. Bream RN. Jackson PS. Leach AG. Longbottom DA. Nesi M. Scott JS. Storer RI. Taylor SJ. J. Chem. Soc., Perkin Trans. 1 2000, 3815

47 Han Y. Walker SD. Young RN. Tetrahedron Lett. 1996, 37: 2703

48 Lee Y. Silverman RB. Tetrahedron 2001, 57: 5339

49 Plunkett MJ. Ellman JA. J. Org. Chem. 1997, 62: 2885

50 Spivey AC. Diaper CM. Adams H. Rudge AJ.
J. Org. Chem. 2000, 65: 5253

51 Rasmussen LK. Begtrup M. Ruhland T. J. Org. Chem. 2006, 71: 1230

52a The Handbook of Radiopharmaceuticals: Radiochemistry and Applications Welch MJ. Redvanly CS. Wiley; New York: 2002.

52b Langen K.-J. Ziemons K. Kiwit JCW. Herzog H. Kuwert T. Bock WJ. Stocklin G. Feinendegen LE. Muller-Gartner H.-W. J. Nucl. Med. 1997, 38: 517

52c Weber W. Bartenstein P. Gross MW. Kinzel D. Daschner H. Feldmann HJ. Reidel G. Ziegler SI. Lumenta C. Molls M. Schwaiger M. J. Nucl. Med. 1997, 38: 802

53 Young JK. Nelson JC. Moore JS. J. Am. Chem. Soc. 1994, 116: 10841

54a Nelson JC. Young JK. Moore JS. J. Org. Chem. 1996, 61: 8160

54b Zhang JS. Moore JS. Xu ZF. Aguirre RA. J. Am. Chem. Soc. 1992, 114: 2273

55 Jones L. Schumm JS. Tour JM. J. Org. Chem. 1997, 62: 1388

56 Hunt JA. Roush WR. J. Am. Chem. Soc. 1996, 118: 9998

57 Takahashi T. Tomida S. Inoue H. Doi T. Synlett 1998, 1261

58 Creed D. Caldwell RA. Hiroyuki O. DeMarco DC.
J. Am. Chem. Soc. 1977, 99: 278

59 Xu W.-M. Wang Y.-G. Miao M.-Z. Huang X. Synthesis 2005, 2143

60 Sheng SR. Hu MG. Xin Q. Liu XL. Huang X. Chin. Chem. Lett. 2007, 18: 377

61 Flanagan RJ. inventors; PCT US Appl. US 4874601.

62a Yong L. Yao M.-L. Kelly H. Green JF. Kabalka GW. Chem. Commun. 2010, 46: 2623

62b Yong L. Yao M.-L. Kelly H. Green JF. Kabalka GW. J. Labelled Compd. Radiopharm. 2011, 54: 173

63 Kawai K. Ohta H. Channing MA. Kubodera A. Eckelman WC. Appl. Radiat. Isot. 1996, 47: 37

64 Brown SD. Armstrong RW. J. Org. Chem. 1997, 62: 7076

65 Hunter DH. Culbert PA. Reactive Polymers 1993, 19: 247

66a Hunter DH. Zhu X. J. Labelled Compd. Radiopharm. 1999, 42: 653

66b Hunter DH, and Zhu X. inventors; PCT Int. Appl. WO 18053.

67 Kuschel S. Shea C. Fowler JS. Gifford AN. Bioconjugate Chem. 2011, 22: 406

68 Kabalka GW. Namboodiri V. Akula MR. J. Labelled Compd. Radiopharm. 2001, 44: 921

69a Donovan A. Forbes J. Dorff P. Schaffer P. Babich J. Valliant JF. J. Am. Chem. Soc. 2006, 128: 3536

69b Valliant JF, Dorff P, and Chirakal R. inventors; PCT Int. Appl. WO 035744 A2.

69c Valliant JF, Dorff P, and Chirakal R. inventors; PCT US Appl. US 0005545 A1.

70 Donovan AC. Valliant JF. J. Org. Chem. 2009, 74: 8133

71 Donovan AC. Valliant JF. Nucl. Med. Biol. 2008, 35: 741

72 McIntee JW. Sundararajan C. Donovan AC. Kovacs MS. Capretta A. Valliant JF. J. Org. Chem. 2008, 73: 8236