Download PDF
Jamison, T. F. et al.: 2018 Science of Synthesis, 2018/5: Flow Chemistry in Organic Synthesis DOI: 10.1055/sos-SD-228-00177
Flow Chemistry in Organic Synthesis

9 Immobilized Reagents and Multistep Processes

More Information

Book

Editors: Jamison, T. F.; Koch, G.

Authors: Beeler, A. B.; Beingessner, R. L.; Bottecchia, C.; Browne, D. L.; Coley, C. W.; Ferguson, S.; Folgueiras-Amador, A. A.; Gilmore, K.; Hicklin, R. W.; Imbrogno, J.; Itsuno, S.; Jamison, T. F.; Jensen, K. F.; Kelly, L. P.; Kerr, M. S.; Kiesman, W. F.; Kim, H.; Kwok, D.-I. A.; Ley, S. V.; Longstreet, A. R.; May, S. A. ; McTeague, T. A.; Mijalis, A. J.; Mo, Y.; Moon, S.; Myerson, A.; Noël, T.; O’Brien, A. G.; O’Brien, M.; O’Mahony, M.; Opalka, S. M.; Pentelute, B. L.; Polyzos, A. ; Schepartz, A.; Seeberger, P. H.; Seo, H.; Steinauer, A.; Stelzer, T.; Stephenson, C. R. J.; Strom, A. E.; Styduhar, E. D.; Sun, A. C.; Telmesani, R.; Thomas, D. A.; Tran, T. H.; Ullah, M. S.; Wicker, A. C.; Wirth, T.; Yoshida, J.

Title: Flow Chemistry in Organic Synthesis

Print ISBN: 9783132423312; Online ISBN: 9783132423350; Book DOI: 10.1055/b-006-161272

1st edition © 2018. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner (Editor-in-Chief), A.; Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

Also available at
 


Abstract

Multistep continuous-flow processing enables the direct preparation of complex chemical materials from simple input streams through a series of complexity-adding reaction steps. The use of polymer-supported reagents can greatly facilitate this process through the inline hosting of reagents or catalysts, the scavenging of spent materials or impurities, or even the temporary hosting of reactive intermediates prior to their reaction and release from the support. This chapter provides a comprehensive overview of such polymer-supported techniques.

Key words

Keywords: - polymer-supported reagents - multistep flow synthesis - natural products - pharmaceutical agents - catch and release
 
  • 1 McKillop A, Young DW. Synthesis 1979; 401
  • 2 McKillop A, Young DW. Synthesis 1979; 481
  • 3 Shuttleworth SJ, Allin SM, Sharma PK. Synthesis 1997; 1217
  • 4 Shuttleworth SJ, Allin SM, Wilson RD, Nasturica D. Synthesis 2000; 1035
  • 5 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
  • 6 Sussman S. Ind. Eng. Chem 1946; 38: 1228
  • 7 Smil V. Nature (London) 1999; 400: 415
  • 8 Ley SV, Baxendale IR. Nat. Rev. Drug Discovery 2002; 1: 573
  • 9 Wegner J, Celan S, Kirschning A. Adv. Synth. Catal 2012; 354: 17
  • 10 Moore JS, Jensen KF. Angew. Chem. Int. Ed 2014; 53: 470
  • 11 Webb D, Jamison TF. Chem. Sci 2010; 1: 675
  • 12 Wirth T. ChemSusChem 2013; 5: 215
  • 13 Hartman RL, McMullen JP, Jensen KF. Angew. Chem. Int. Ed 2011; 50: 7502
  • 14 Ingham RJ, Battilocchio C, Fitzpatrick DE, Sliwinski E, Hawkins JM, Ley SV. Angew. Chem. Int. Ed 2015; 54: 144
  • 15 Mascia S, Heider PL, Zhang H, Lakerveld R, Benyahia B, Barton PI, Braatz RD, Cooney CL, Evans JMB, Jamison TF, Jensen KF, Myerson AS, Trout BL. Angew. Chem. Int. Ed 2013; 52: 12359
  • 16 Hopkin MD, Baxendale IR, Ley SV. Org. Biomol. Chem 2013; 11: 1822
  • 17 Adamo A, Beingessner RL, Behnam M, Chen J, Jamison TF, Jensen KF, Monbaliu J.-CM, Myerson AS, Revalor EM, Snead DR, Stelzer T, Weeranoppanant N, Wong SY, Zhang P. Science (Washington, D. C.) 2016; 352: 61
  • 18 Fitzpatrick DE, Ley SV. React. Chem. Eng 2016; 1: 629
  • 19 Carmona-Vargas CC, Alves LdeC, Brocksom TJ, de Oliveira KT. React. Chem. Eng 2017; 2: 366
  • 20 Ley SV, Fitzpatrick DE, Myers RM, Battilocchio C, Ingham RJ. Angew. Chem. Int. Ed 2015; 54: 10122
  • 21 Anastas PT, Warner JC. Green Chemistry: Theory and Practice. Oxford University Press; Oxford, UK 1998
    Google Scholar
  • 22 Ley SV, Fitzpatrick DE, Ingham RJ, Myers RM. Angew. Chem. Int. Ed 2015; 54: 3449
  • 23 Cervera-Padrell AE, Nielsen JP, Jønch Pedersen M, Müller Christensen K, Mortensen AR, Skovby T, Dam-Johansen K, Kiil S, Gernaey KV. Org. Process Res. Dev 2012; 16: 901
  • 24 Skilton RA, Bourne RA, Amara Z, Horvath R, Jin J, Scully MJ, Streng E, Tang SLY, Summers PA, Wang J, Pérez E, Asfaw N, Aydos GLP, Dupont J, Comak G, George MW, Poliakoff M. Nat. Chem 2015; 7: 1
  • 25 Fitzpatrick DE, Battilocchio C, Ley SV. Org. Process Res. Dev 2016; 20: 386
  • 26 Bonfils F, Cazaux I, Hodge P, Caze C. Org. Biomol. Chem 2006; 4: 493
  • 27 Storer RI, Takemoto T, Jackson PS, Ley SV. Angew. Chem. Int. Ed 2003; 42: 2521
  • 28 Sherington DC. J. Polym. Sci., Part A: Polym. Chem 2001; 39: 2364
  • 29 Drewy DH, Coe DM, Poon S. Med. Res. Rev 1999; 19: 97
  • 30 Akelah A, Sherington DC. Polymer 1983; 24: 1369
  • 31 Holmes N, Akien GR, Savage RJD, Stanetty C, Baxendale IR, Blacker AJ, Taylor BA, Woodward RL, Meadows RE, Bourne RA. React. Chem. Eng 2016; 1: 96
  • 32 Ley SV, Ingham RJ, OʼBrien M, Browne DL. Beilstein J. Org. Chem 2013; 9: 1051
  • 33 Qian Z, Baxendale IR, Ley SV. Synlett 2010; 505
  • 34 de Miranda AS, Silva MVdeM, Dias FC, de Souza SP, Leão RAC, de Souza ROMA. React. Chem. Eng 2017; 2: 375
  • 35 Guetzoyan L, Nikbin N, Baxendale IR, Ley SV. Chem. Sci 2013; 4: 764
  • 36 Desai B, Dixon K, Farrant E, Feng Q, Gibson KR, van Hoorn WP, Mills J, Morgan T, Parry DM, Ramjee MK, Selway CN, Tarver GJ, Whitlock G, Wright AG. J. Med. Chem 2013; 56: 3033
  • 37 Ley SV, Bolli M, Hinzen B, Gervois A.-G, Hall B, Habermann J, Scott J, Haunert F. WO 9 958 475, 1999
  • 38 Mallia CJ, Baxendale IR. Org. Process Res. Dev 2016; 20: 327
  • 39 Brozowski M, OʼBrien M, Ley SV, Polyzos A. Acc. Chem. Res 2015; 48: 349
  • 40 Su Y, Straathof NJW, Hessel V, Noël T. Chem.–Eur. J 2014; 20: 10562
  • 41 Arai K, Wirth T. Org. Process Res. Dev 2014; 18: 1377
  • 42 Kuleshova J, Hill-Cousins JT, Birkin PR, Brown RCD, Pletcher D, Underwood TJ. Electrochim. Acta 2012; 69: 197
  • 43 Browne DL, Deadman BJ, Ashe R, Baxendale IR, Ley SV. Org. Process Res. Dev 2011; 15: 693
  • 44 Deadman BJ, Browne DL, Baxendale IR, Ley SV. Chem. Eng. Technol 2015; 38: 259
  • 45 OʼBrien M, Koos P, Browne DL, Ley SV. Org. Biomol. Chem 2012; 10: 7031
  • 46 Adamo A, Heider PL, Weeranoppanant N, Jensen KF. Ind. Eng. Chem. Res 2013; 52: 10802
  • 47 Ingham RJ, Battilocchio C, Hawkins JM, Ley SV. Beilstein J. Org. Chem 2014; 10: 641
  • 48 Carter CF, Lange H, Ley SV, Baxendale IR, Wittkamp B, Goode JG, Gaunt NL. Org. Process Res. Dev 2010; 14: 393
  • 49 Lange H, Carter CF, Hopkin MD, Burke A, Goode JG, Baxendale IR, Ley SV. Chem. Sci 2011; 2: 765
  • 50 Hafner A, Ley SV. Synlett 2015; 26: 1470
  • 51 Baxendale IR, Griffiths-Jones CM, Ley SV, Tranmer GK. Chem.–Eur. J 2006; 12: 4407
  • 52 Che H, van Hest JCM. J. Mater. Chem. B 2016; 4: 4632
  • 53 Hübner J, Heinzler CA, Hohmann S, Brenner-Weiß G, Franzreb M. React. Chem. Eng 2017; 2: 349
  • 54 Baxendale IR, Schou SC, Sedelmeier J, Ley SV. Chem.–Eur. J 2010; 16: 89
  • 55 Švec F, Fréchet JMJ. Anal. Chem 1992; 64: 820
  • 56 Kirschning A, Altwicker C, Dräger G, Harders J, Hoffmann N, Hoffmann U, Schönfeld H, Solodenko W, Kunz U. Angew. Chem. Int. Ed 2001; 40: 3995
  • 57 Kunz U, Schönfeld H, Kirschning A, Solodenko W. J. Chromatogr., A 2003; 1006: 241
  • 58 Solodenko W, Wen H, Leue S, Stuhlmann F, Sourkouni-Argirusi G, Jas G, Schönfeld H, Kunz U, Kirschning A. Eur. J. Org. Chem 2004; 3601
  • 59 Roper KA, Lange H, Polyzos A, Berry MB, Baxendale IR, Ley SV. Beilstein J. Org. Chem 2011; 7: 1648
  • 60 Smith CJ, Smith CD, Nikbin N, Ley SV, Baxendale IR. Org. Biomol. Chem 2011; 9: 1927
  • 61 Baumann M, Baxendale IR, Ley SV, Smith CD, Tranmer GK. Org. Lett 2006; 8: 5231
  • 62 Baxendale IR, Ley SV, Mansfield AC, Smith CD. Angew. Chem. Int. Ed 2009; 48: 4017
  • 63 Deadman BJ, Battilocchio C, Sliwinski E, Ley SV. Green Chem 2013; 15: 2050
  • 64 Brahma A, Musio B, Ismayilova U, Nikbin N, Kamptmann SB, Siegert P, Jeromin GE, Ley SV, Pohl M. Synlett 2016; 27: 262
  • 65 Glasnov TN, Kappe CO. Adv. Synth. Catal 2010; 352: 3089
  • 66 Correia CA, Gilmore K, McQuade DT, Seeberger PH. Angew. Chem. Int. Ed 2015; 54: 4945
  • 67 Longstreet AR, Opalka SM, Campbell BS, Gupton BF, McQuade DT. Beilstein J. Org. Chem 2013; 9: 2570
  • 68 Lau S.-H, Bourne SL, Martin B, Schenkel B, Penn G, Ley SV. Org. Lett 2015; 17: 5436
  • 69 Baxendale IR, Deeley J, Griffiths-Jones CM, Ley SV, Saaby S, Tranmer GK. Chem. Commun. (Cambridge) 2006; 2566
  • 70 Baxendale IR, Griffiths-Jones CM, Ley SV, Tranmer GK. Synlett 2006; 427
  • 71 Riva E, Rencurosi A, Gagliardi S, Passarella D, Martinelli M. Chem.–Eur. J 2011; 17: 6221
  • 72 Brasholz M, Macdonald JM, Saubern S, Ryan JH, Holmes AB. Chem.–Eur. J 2010; 16: 11471
  • 73 Baumann M, Baxendale IR, Brasholz M, Hayward JJ, Ley SV, Nikbin N. Synlett 2011; 1375
  • 74 Newton S, Carter CF, Pearson CM, Alves LdeC, Lange H, Thansandote P, Ley SV. Angew. Chem. Int. Ed 2014; 53: 4915