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

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

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

Further Information

Publication History

Received 23 August 2011
Publication Date:
08 November 2011 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

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

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

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

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

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

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

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

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

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

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

Google Scholar
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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Google Scholar
For reviews on fluorous-phase synthesis see:
7a Zhang W. Tetrahedron 2003, 59: 4475

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

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

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

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

Google Scholar
7f Curran DP. Science 2008, 321: 1645

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Google Scholar
17 Olah GA. Li XY. Synlett 1990, 267

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Google Scholar
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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Google Scholar