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Wang, M.  et al.: Science of Synthesis: Knowledge Updates 2024/3 DOI: 10.1055/sos-SD-122-00258

22.7.2.2 Ortho Esters and Halogenated Derivatives (Update 2024)

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Book

Editors: Wang, M. ; Drabowicz, J. ; Jiang, X. ; Campagne, J.-M. 

Authors: Gulder, T. ; Kretzschmar, M. ; Marciniszyn, J. P.; Kiełbasiński, P. ; Kwiatkowska, M. ; Zhu, H. ; Fan, Q. ; Mita, T. ; Rawat, V. K. ; Favre-Réguillon, A. ; Leclerc, E. 

Title: Knowledge Updates 2024/3

Online ISBN: 9783132457089; Book DOI: 10.1055/b000000969

early view © Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

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

Science of Synthesis Knowledge Updates



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); 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

This review is an update to the earlier Science of Synthesis contribution (Section 22.7.2) and describes methods for the formation of ortho esters and halogenated derivatives reported in the period 2005–2023. The first part focuses on recent advances in the synthesis of 1,1-dihalogenated ethers and 1-halogenated acetals. The second part of this review covers the latest synthetic strategies to access various functional ortho esters.

Key words

ortho esters - halogenated ethers - halogenated acetals - radical reactions - transition-metal catalysis - electrochemistry - nucleophilic substitution - tandem cyclizations - rearrangement reactions
 
  • 1 Lebel H, Grenon M. Science of Synthesis 2005; 22: 669
  • 2 Kharasch MS, Friedlander HN. J. Org. Chem. 1949; 14: 239
    PubMed
  • 3 Warashina T, Matsuura D, Sengoku T, Takahashi M, Yoda H, Kimura Y. Org. Process Res. Dev. 2019; 23: 614
  • 4 Kimura Y, Warashina T. Tetrahedron Lett. 2017; 58: 4598
  • 5 Dolbier Jr WR, Wang F, Tang X, Thomoson CS, Wang L. J. Fluorine Chem. 2014; 160: 72
  • 6 Fier PS, Hartwig JF. Angew. Chem. Int. Ed. 2013; 52: 2092
    PubMed
  • 7 Li L, Wang F, Ni C, Hu J. Angew. Chem. Int. Ed. 2013; 52: 12390
    PubMed
  • 8 Thomoson CS, Dolbier Jr WR. J. Org. Chem. 2013; 78: 8904
    PubMed
  • 9 Zafrani Y, Sod-Moriah G, Segall Y. Tetrahedron 2009; 65: 5278
  • 10 Zhang L, Zheng J, Hu J. J. Org. Chem. 2006; 71: 9845
    PubMed
  • 11 Zheng J, Li Y, Zhang L, Hu J, Meuzelaar GJ, Federsel H.-J. Chem. Commun. (Cambridge) 2007; 5149
    PubMed
  • 12 Bao Y, Wang G.-Y, Zhang Y.-X, Bian K.-J, Wang X.-S. Chem. Sci. 2018; 9: 2986
    PubMed
  • 13 Newton J, Driedger D, Nodwell MB, Schaffer P, Martin RE, Britton R, Friesen CM. Chem.–Eur. J. 2019; 25: 15993
    PubMed
  • 14 Chatalova-Sazepin C, Binayeva M, Epifanov M, Zhang W, Foth P, Amador C, Jagdeo M, Boswell BR, Sammis GM. Org. Lett. 2016; 18: 4570
    PubMed
  • 15 Newton JJ, Brooke AJ, Duhamel B, Pulfer JM, Britton R, Friesen CM. J. Org. Chem. 2020; 85: 13298
    PubMed
  • 16 Hagooly Y, Rozen S. J. Org. Chem. 2008; 73: 6780
    PubMed
  • 17 Smela MP, Hoye TR. Org. Lett. 2018; 20: 5502
    PubMed
  • 18 Zhou Z, Cao C, Yin Z, Liu Q. Org. Lett. 2009; 11: 1781
    PubMed
  • 19 Saint-Jalmes L. J. Fluorine Chem. 2006; 127: 85
  • 20 Thomas HG, Schmitz A. Synthesis 1985; 31
  • 21 Scheeren JW, Goossens HJM, Top AWH. Synthesis 1978; 283
  • 22 Röckl JL, Hauck AV, Schollmeyer D, Waldvogel SR. ChemistryOpen 2019; 8: 1167
    PubMed
  • 23 Garcia AD, Leech MC, Petti A, Denis C, Goodall ICA, Dobbs AP, Lam K. Org. Lett. 2020; 22: 4000
    PubMed
  • 24 Kantlehner W, Maier T, Kapassakalidis JJ. Liebigs Ann. Chem. 1981; 70
  • 25 Kantlehner W, Vettel M, Eppinger B. Z. Naturforsch., B 2012; 67: 373
  • 26 Noè M, Perosa A, Selva M. Green Chem. 2013; 15: 2252
  • 27 Yamada K, Ishiyama S, Onizuka K, Nagatsugi F. Tetrahedron 2017; 73: 1424
  • 28 Yang M, Larson PG, Brown L, Schultz JR, Kucaba TA, Griffith TS, Ferguson DM. Bioorg. Med. Chem. Lett. 2022; 59: 128548
  • 29 Cortigiani M, Mereu A, Healy MG, Adamo MFA. J. Org. Chem. 2019; 84: 4112
    PubMed
  • 30 By K, Nantz MH. Angew. Chem. Int. Ed. 2004; 43: 1117
    PubMed
  • 31 Cosgrove KL, McGeary RP. Synlett 2008; 2425
  • 32 Yasukawa N, Kanie T, Kuwata M, Monguchi Y, Sajiki H, Sawama Y. Chem.–Eur. J. 2017; 23: 10974
    PubMed
  • 33 Peil S, González AG, Leutzsch M, Fürstner A. J. Am. Chem. Soc. 2022; 144: 4158
    PubMed
  • 34 Venneri PC, Warkentin J. Can. J. Chem. 2000; 78: 1194
  • 35 Dawid M, Warkentin J. Can. J. Chem. 2003; 81: 598
  • 36 Pole DL, Warkentin J. J. Org. Chem. 1997; 62: 4065
  • 37 Dawid M, Mloston G, Warkentin J. Chem.–Eur. J. 2002; 8: 2184
    PubMed
  • 38 Croisetière J.-P, Spino C. J. Org. Chem. 2018; 83: 5609 J. Org. Chem., 2018; 83: 6824
    PubMed
  • 39 Tanabe H, He X, Kothandaraman P, Yamane M. Synlett 2010; 1190
  • 40 Kato K, Teraguchi R, Motodate S, Uchida A, Mochida T, Peganova TA, Vologdin NV, Akita H. Chem. Commun. (Cambridge) 2008; 3687
    PubMed
  • 41 Ma R, Chen Y, Fang S, Jiang H, Yang S, Wu W. Chem. Commun. (Cambridge) 2022; 58: 13907
    PubMed
  • 42 Kusakabe T, Kato K. Tetrahedron 2011; 67: 1511
  • 43 Kato K, Teraguchi R, Kusakabe T, Motodate S, Yamamura S, Mochida T, Akita H. Synlett 2007; 63
  • 44 Fukuhara T, Hasegawa C, Hara S. Synthesis 2007; 1528
  • 45 Tange S, Fukuhara T, Hara S. Synthesis 2008; 3219
  • 46 Huang Z, Derksen DJ, Vederas JC. Org. Lett. 2010; 12: 2282
    PubMed
  • 47 Giner J.-L. Org. Lett. 2005; 7: 499
    PubMed
  • 48 Petroski RJ. Org. Commun. 2008; 1: 48
  • 49 La Cruz TE, Rychnovsky SD. Synlett 2004; 2013
  • 50 Meerwein H, Bodenbenner K, Borner P, Kunert F, Müller KW, Sasse HJ, Schrodt H, Spille J. Angew. Chem. 1955; 67: 374
  • 51 Kas’yan LI, Tarabara IN, Kas’yan AO. Russ. J. Org. Chem. (Engl. Transl.) 2004; 40: 1227
  • 52 Ahmed A, Christie SDR, Elsegood MRJ, Pritchard GJ. Chem. Commun. (Cambridge) 2013; 49: 7489
    PubMed
  • 53 Otto S, Furlan RLE, Sanders JKM. Science (Washington, D. C.) 2002; 297: 590
    PubMed
  • 54 Herrmann A. Chem. Soc. Rev. 2014; 43: 1899
    PubMed
  • 55 Ramström O, Lehn J.-M. Nat. Rev. Drug Discovery 2002; 1: 26
    PubMed
  • 56 Mondal M, Radeva N, Köster H, Park A, Potamitis C, Zervou M, Klebe G, Hirsch AKH. Angew. Chem. Int. Ed. 2014; 53: 3259
    PubMed
  • 57 Ayme J.-F, Beves JE, Leigh DA, McBurney RT, Rissanen K, Schultz D. Nat. Chem. 2012; 4: 15
  • 58 Ponnuswamy N, Cougnon FBL, Clough JM, Pantoş GD, Sanders JKM. Science (Washington, D. C.) 2012; 338: 783
    PubMed
  • 59 You L, Berman JS, Anslyn EV. Nat. Chem. 2011; 3: 943
    PubMed
  • 60 Askim JR, Mahmoudi M, Suslick KS. Chem. Soc. Rev. 2013; 42: 8649
    PubMed
  • 61 Teichert JF, Mazunin D, Bode JW. J. Am. Chem. Soc. 2013; 135: 11314
    PubMed
  • 62 Ding S.-Y, Wang W. Chem. Soc. Rev. 2013; 42: 548
    PubMed
  • 63 Brachvogel R.-C, von Delius M. Chem. Sci. 2015; 6: 1399
    PubMed
  • 64 Karanfil A, Eskici M. Synth. Commun. 2017; 47: 2342
  • 65 Bunse P, Würthwein E.-U, Wünsch B. Eur. J. Org. Chem. 2018; 1806
  • 66 Song D, Sun S, Tian Y, Huang S, Ding Y, Yuan Y, Hu A. J. Mater. Chem. B 2015; 3: 3195
    PubMed