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

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Synthesis 2011(24): 3929-3953
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

Weitere Informationen

Publikationsverlauf

Received 23 August 2011
Publikationsdatum:
08. November 2011 (online)

Abstract
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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

References

For reviews on solid-phase synthesis see:
1a Guillier F. Orain D. Bradley M. Chem. Rev. 2000, 100: 2091

Suche in Google Scholar
1b Bräse S. Dahmen S. Chem. Eur. J. 2000, 6: 1899

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

Suche in Google Scholar
1d Bräse S. Acc. Chem. Res. 2004, 37: 805

Suche in Google Scholar
1e Scott PJH. Steel PG. Eur. J. Org. Chem. 2006, 2251
1f Merrifield RB. J. Am. Chem. Soc. 1963, 85: 2149

Suche in Google Scholar
2a Gribble GW. Acc. Chem. Res. 1998, 31: 141

Suche in Google Scholar
2b Gribble GW. J. Chem. Educ. 2004, 81: 1441

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

Suche in Google Scholar
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

Suche in Google Scholar
3b Müller K. Faeh C. Diederich F. Science 2007, 317: 1881

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

Suche in Google Scholar
3d Hagmann WK. J. Med. Chem. 2008, 51: 4359

Suche in Google Scholar
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

Suche in Google Scholar
4d Fairlamb I. Chem. Soc. Rev. 2007, 36: 1036

Suche in Google Scholar
4e Amii H. Uneyama K. Chem. Rev. 2009, 109: 2119

Suche in Google Scholar
For reviews on molecular imaging see:
5a Kugaya A. Fujita M. Innis RB. Ann. Nucl. Med. 2000, 14: 1

Suche in Google Scholar
5b Schyler DJ. Ann. Acad. Med. Singapore 2004, 33: 146

Suche in Google Scholar
5c Wester H.-J. Clin. Cancer Res. 2007, 13: 3470

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

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

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

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

Suche in Google Scholar
5h Janjic JM. Ahrens ET. WIREs Nanomed. Nanobio. 2009, 1: 492

Suche in Google Scholar
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

Suche in Google Scholar
7b Zhang W. Chem. Rev. 2004, 104: 2531

Suche in Google Scholar
7c Dandapani S. QSAR Comb. Sci. 2006, 25: 681

Suche in Google Scholar
7d Zhang W. Curran DP. Tetrahedron 2006, 62: 11837

Suche in Google Scholar
7e Zhang W. Cai C. Chem. Commun. 2008, 5686
7f Curran DP. Science 2008, 321: 1645

Suche in Google Scholar
7g Zhang W. Chem. Rev. 2009, 109: 749

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

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

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

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

Suche in Google Scholar
For reviews of ^¹8F-radiochemistry see:
9a Schirrmacher R. Wängler C. Schirrmacher E. Mini-Rev. Org. Chem. 2007, 4: 317

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

Suche in Google Scholar
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

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

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

Suche in Google Scholar
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

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

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

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

Suche in Google Scholar
17 Olah GA. Li XY. Synlett 1990, 267
18 Sket B. Zupan M. Zupet P. Tetrahedron 1984, 40: 1603

Suche in Google Scholar
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

Suche in Google Scholar
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

Suche in Google Scholar
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

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

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

Suche in Google Scholar
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

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

Suche in Google Scholar
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

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

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

Suche in Google Scholar
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

Suche in Google Scholar
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

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

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

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

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

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

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

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

Suche in Google Scholar
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

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

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

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

Suche in Google Scholar
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

Suche in Google Scholar
42i Pacheco MC. Gouverneur V. Org. Lett. 2005, 7: 1267

Suche in Google Scholar
42j Greedy B. Gouverneur V. Chem. Commun. 2001, 233
43 Pilot C. Dahmen S. Lauterwasser F. Bräse S. Tetrahedron Lett. 2001, 42: 9179

Suche in Google Scholar
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

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

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

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

Suche in Google Scholar
46a Zajc B. Zupan M. Tetrahedron 1989, 45: 7869

Suche in Google Scholar
46b Zupan M. Šegatin N. Synth. Commun. 1994, 24: 2617

Suche in Google Scholar
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

Suche in Google Scholar
48 Lee Y. Silverman RB. Tetrahedron 2001, 57: 5339

Suche in Google Scholar
49 Plunkett MJ. Ellman JA. J. Org. Chem. 1997, 62: 2885

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

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

Suche in Google Scholar
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

Suche in Google Scholar
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

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

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

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

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

Suche in Google Scholar
56 Hunt JA. Roush WR. J. Am. Chem. Soc. 1996, 118: 9998

Suche in Google Scholar
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

Suche in Google Scholar
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

Suche in Google Scholar
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

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

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

Suche in Google Scholar
64 Brown SD. Armstrong RW. J. Org. Chem. 1997, 62: 7076

Suche in Google Scholar
65 Hunter DH. Culbert PA. Reactive Polymers 1993, 19: 247

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

Suche in Google Scholar
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

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

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

Suche in Google Scholar
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

Suche in Google Scholar
71 Donovan AC. Valliant JF. Nucl. Med. Biol. 2008, 35: 741

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

Suche in Google Scholar