PDF herunterladen
Ackermann, L. : 2022 Science of Synthesis, 2021/5: Electrochemistry in Organic Synthesis DOI: 10.1055/sos-SD-236-00167
Electrochemistry in Organic Synthesis

9 Anodic Arylation Reactions

Weitere Informationen

Buch

Herausgeber: Ackermann, L. 

Autoren: Ackermann, L. ; Brown, R. C. D. ; Enders, P.; Fang, P.; Folgueiras-Amador, A. A. ; Francke, R. ; Galczynski, J.; Gosmini, C. ; Hodgson, J. W.; Hou, Z.-W.; Huang, H.; Huang, Z.; Inagi, S. ; Kuciński, K. ; Kuriyama, M. ; Lam, K. ; Lambert, T. H.; Leech, M. C. ; Lennox, A. J. J. ; Lin, Z.; Little, R. D.; Massignan, L.; Mei, T.-S.; Meyer, T. H.; Moeller, K. D. ; Onomura, O. ; Prudlik, A.; Ruan, Z. ; Scheremetjew, A. ; Schiltz, P.; Selt, M.; Villani, E. ; Waldvogel, S. R. ; Wang, Z.-H.; Wu, T.; Xing, Y.-K.; Xu, H.-C. ; Yamamoto, K. 

Titel: Electrochemistry in Organic Synthesis

Print ISBN: 9783132442122; Online ISBN: 9783132442146; Buch-DOI: 10.1055/b000000126

1st edition © 2022. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

Science of Synthesis Reference Libraries



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Reihenherausgeber: 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.

Typ: Mehrbändiges Werk

Auch verfügbar auf
 


Abstract

The arylation of organic compounds is a tremendously important tool in organic synthesis, since substituted (het)arenes are essential moieties in many applications ranging from organic intermediates to natural products, pharmaceuticals, and materials. Therefore, an effective, sustainable, and economic synthetic accesses to such compounds is of great demand. This chapter covers the arylation of carbon and heteroatom compounds via an electrooxidative pathway. Direct dehydrogenative methods without the application of a metal catalyst as well as constant-current electrolyses are emphasized. The electrochemical synthesis of biaryl compounds, arylalkanes and arylalkenes, as well as arylated nitrogen, oxygen, and sulfur compounds are described in detail. Additionally, the synthesis of heterocycles through anodic arylation reactions is discussed.

Schlüsselwörter

organic electrochemistry - electrosynthesis - anodic oxidation - arylation - aromatic compounds - heteroaromatic compounds - biaryls - arylalkenes - arylalkanes - arylamines - phenols - sulfides - sulfones - sulfonates - sulfonamides - sulfonimides - benzofurans - dibenzopyranones - indoles - carbazoles - benzimidazoles - benzoxazoles - benzothiazoles - benzoxazines - phenanthridinones
 
  • 2 Nelson TD, Crouch RD. Org. React. (N. Y.) 2004; 63: 265
  • 3 Beletskaya IP, Cheprakov AV. Chem. Rev. 2000; 100: 3009
    PubMed
  • 4 Tamao K, Sumitani K, Kumada M. J. Am. Chem. Soc. 1972; 94: 4374
  • 5 Chinchilla R, Nájera C. Chem. Soc. Rev. 2011; 40: 5084
    PubMed
  • 6 Baba S, Negishi E. J. Am. Chem. Soc. 1976; 98: 6729
  • 7 Stille JK. Angew. Chem. 1986; 98: 504 Angew. Chem. Int. Ed. 1986; 25: 508
  • 8 Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
  • 9 Anastas P, Eghbali N. Chem. Soc. Rev. 2010; 39: 301
    PubMed
  • 10 Frontana-Uribe BA, Little RD, Ibanez JG, Palma A, Vasquez-Medrano R. Green Chem. 2010; 12: 2099
  • 11 Schäfer HJ. C. R. Chim. 2011; 14: 745
  • 12 Handbook of C—H Transformations: Applications in Organic Synthesis. Dyker G. Wiley-VCH; Weinheim, Germany 2005
    CrossrefGoogle Scholar
  • 13 Waldvogel SR, Lips S, Selt M, Riehl B, Kampf CJ. Chem. Rev. 2018; 118: 6706
    PubMed
  • 14 Negishi E. Angew. Chem. 2011; 123: 6870 Angew. Chem. Int. Ed. 2011; 50: 6738
    PubMed
  • 15 Suzuki A. Angew. Chem. 2011; 123: 6854 Angew. Chem. Int. Ed. 2011; 50: 6722
    PubMed
  • 16 Modern Arene Chemistry: Concepts, Synthesis, and Applications. Astruc D. Wiley-VCH; Weinheim, Germany 2002
    CrossrefGoogle Scholar
  • 17 Bringmann G, Gulder T, Gulder TAM, Breuning M. Chem. Rev. 2011; 111: 563
    PubMed
  • 18 Kozlowski MC, Morgan BJ, Linton EC. Chem. Soc. Rev. 2009; 38: 3193
    PubMed
  • 19 von Nussbaum F, Brands M, Hinzen B, Weigand S, Häbich D. Angew. Chem. 2006; 118: 5194 Angew. Chem. Int. Ed. 2006; 45: 5072
    PubMed
  • 20 Magano J, Dunetz JR. Chem. Rev. 2011; 111: 2177
    PubMed
  • 21 Grimsdale AC, Chan KL, Martin RE, Jokisz PG, Holmes AB. Chem. Rev. 2009; 109: 897
    PubMed
  • 22 Kirsch P, Bremer M. Angew. Chem. 2000; 112: 4384 Angew. Chem. Int. Ed. 2000; 39: 4216
    PubMed
  • 23 Okamoto K, Zhang J, Housekeeper JB, Marder SR, Luscombe CK. Macromolecules 2013; 46: 8059
  • 24 Cortez GA, Schrock RR, Hoveyda AH. Angew. Chem. 2007; 119: 4618 Angew. Chem. Int. Ed. 2007; 46: 4534
    PubMed
  • 25 Franke R, Selent D, Börner A. Chem. Rev. 2012; 112: 5675
    PubMed
  • 26 van Leeuwen PWNM, Kamer PCJ, Claver C, Pàmies O, Diéguez M. Chem. Rev. 2011; 111: 2077
    PubMed
  • 27 Corbet J.-P, Mignani G. Chem. Rev. 2006; 106: 2651
    PubMed
  • 28 Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev. 2002; 102: 1359
    PubMed
  • 29 Stanforth SP. Tetrahedron 1998; 54: 263
  • 30 Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
    PubMed
  • 31 Aiso H, Kochi T, Mutsutani H, Tanabe T, Nishiyama S, Kakiuchi F. J. Org. Chem. 2012; 77: 7718
    PubMed
  • 32 Amatore C, Cammoun C, Jutand A. Eur. J. Org. Chem. 2008; 4567
  • 33 Mitsudo K, Shiraga T, Kagen D, Shi D, Becker JY, Tanaka H. Tetrahedron 2009; 65: 8384
  • 34 Mitsudo K, Shiraga T, Tanaka H. Tetrahedron Lett. 2008; 49: 6593
  • 35 Beil SB, Müller T, Sillart SB, Franzmann P, Bomm A, Holtkamp M, Karst U, Schade W, Waldvogel SR. Angew. Chem. 2018; 130: 2475 Angew. Chem. Int. Ed. 2018; 57: 2450
    PubMed
  • 36 Boden N, Bushby RJ, Cooke G, Lozman OR, Lu Z. J. Am. Chem. Soc. 2001; 123: 7915
    PubMed
  • 37 Schopohl MC, Siering C, Kataeva O, Waldvogel SR. Angew. Chem. Int. Ed. 2003; 42: 2620
    PubMed
  • 38 Rose A, Zhu Z, Madigan CF, Swager TM, Bulović V. Nature (London) 2005; 434: 876
  • 39 Siering C, Kerschbaumer H, Nieger M, Waldvogel SR. Org. Lett. 2006; 8: 1471
    PubMed
  • 40 Regenbrecht C, Waldvogel SR. Beilstein J. Org. Chem. 2012; 8: 1721
    PubMed
  • 41 Kirste A, Nieger M, Malkowsky IM, Stecker F, Fischer A, Waldvogel SR. Chem.–Eur. J. 2009; 15: 2273
    PubMed
  • 42 Eberson L, Hartshorn MP, Persson O, Radner F. Chem. Commun. (Cambridge) 1996; 2105
  • 43 Hollóczki O, Berkessel A, Mars J, Mezger M, Wiebe A, Waldvogel SR, Kirchner B. ACS Catal. 2017; 7: 1846
  • 44 Selt M, Mentizi S, Schollmeyer D, Franke R, Waldvogel SR. Synlett 2019; 30: 2062
  • 45 Gleede B, Selt M, Franke R, Waldvogel SR. Chem.–Eur. J. 2021; 27: 8252
    PubMed
  • 46 Selt M, Franke R, Waldvogel SR. Org. Process Res. Dev. 2020; 24: 2347
  • 47 Selt M, Gleede B, Franke R, Stenglein A, Waldvogel SR. J. Flow Chem. 2020; 11: 143
  • 48 Malkowsky IM, Rommel CE, Fröhlich R, Griesbach U, Pütter H, Waldvogel SR. Chem.–Eur. J. 2006; 12: 7482
    PubMed
  • 49 Malkowsky IM, Fröhlich R, Griesbach U, Pütter H, Waldvogel SR. Eur. J. Inorg. Chem. 2006; 1690
  • 50 Yoshida J.-i, Shimizu A, Hayashi R. Chem. Rev. 2018; 118: 4702
    PubMed
  • 51 Morofuji T, Shimizu A, Yoshida J.-i. Angew. Chem. 2012; 124: 7371 Angew. Chem. Int. Ed. 2012; 51: 7259
    PubMed
  • 52 Elsler B, Schollmeyer D, Dyballa KM, Franke R, Waldvogel SR. Angew. Chem. 2014; 126: 5311 Angew. Chem. Int. Ed. 2014; 53: 5210
    PubMed
  • 53 Kirste A, Elsler B, Schnakenburg G, Waldvogel SR. J. Am. Chem. Soc. 2012; 134: 3571
    PubMed
  • 54 Elsler B, Wiebe A, Schollmeyer D, Dyballa KM, Franke R, Waldvogel SR. Chem.–Eur. J. 2015; 21: 12321
    PubMed
  • 55 Wiebe A, Schollmeyer D, Dyballa KM, Franke R, Waldvogel SR. Angew. Chem. 2016; 128: 11979 Angew. Chem. Int. Ed. 2016; 55: 11801
    PubMed
  • 56 Wang Q.-Q, Jiang Y.-Y, Zeng C.-C, Sun B.-G. Chin. J. Chem. 2019; 37: 352
  • 57 Schulz L, Enders M, Elsler B, Schollmeyer D, Dyballa KM, Franke R, Waldvogel SR. Angew. Chem. 2017; 129: 4955 Angew. Chem. Int. Ed. 2017; 56: 4877
    PubMed
  • 58 Schulz L, Husmann J.-Å, Waldvogel SR. Electrochim. Acta 2020; 337: 135786
  • 59 Wiebe A, Lips S, Schollmeyer D, Franke R, Waldvogel SR. Angew. Chem. 2017; 129: 14920 Angew. Chem. Int. Ed. 2017; 56: 14727
    PubMed
  • 60 Lielpetere A, Jirgensons A. Eur. J. Org. Chem. 2020; 4510
  • 61 Gütz C, Klöckner B, Waldvogel SR. Org. Process Res. Dev. 2016; 20: 26
  • 62 Amatore C, Cammoun C, Jutand A. Adv. Synth. Catal. 2007; 349: 292
  • 63 Tian J, Moeller KD. Org. Lett. 2005; 7: 5381
    PubMed
  • 64 Baumann AN, Music A, Dechent J, Müller N, Jagau TC, Didier D. Chem.–Eur. J. 2020; 26: 8382
    PubMed
  • 65 Jampilek J. Molecules 2019; 24: 3839
    PubMed
  • 66 Gomtsyan A. Chem. Heterocycl. Compd. (Engl. Transl.) 2012; 48: 7
  • 67 Sakakibara Y, Ito E, Fukushima T, Murakami K, Itami K. Chem.–Eur. J. 2018; 24: 9254
    PubMed
  • 68 Jeanmart S, Edmunds AJF, Lamberth C, Pouliot M. Bioorg. Med. Chem. 2016; 24: 317
    PubMed
  • 69 Newman DJ, Cragg GM. J. Nat. Prod. 2020; 83: 770
    PubMed
  • 70 Guo L, Niu Y, Xu H, Li Q, Razzaque S, Huang Q, Jin S, Tan B. J. Mater. Chem. A 2018; 6: 19775
  • 71 Bowie AL, Hughes CC, Trauner D. Org. Lett. 2005; 7: 5207
    PubMed
  • 72 Amino Group Chemistry: From Synthesis to the Life Sciences. Ricci A. Wiley-VCH; Weinheim, Germany 2008
    Google Scholar
  • 73 Hili R, Yudin AK. Nat. Chem. Biol. 2006; 2: 284
    PubMed
  • 74 MacDiarmid AG. Synth. Met. 1997; 84: 27
  • 75 Bourdelande JL, Gallardo I, Guirado G. J. Am. Chem. Soc. 2007; 129: 2817
    PubMed
  • 76 Morofuji T, Shimizu A, Yoshida J.-i. J. Am. Chem. Soc. 2013; 135: 5000
    PubMed
  • 77 Herold S, Möhle S, Zirbes M, Richter F, Nefzger H, Waldvogel SR. Eur. J. Org. Chem. 2016; 1274
  • 78 Morofuji T, Shimizu A, Yoshida J.-i. J. Am. Chem. Soc. 2015; 137: 9816
    PubMed
  • 79 Hu X, Zhang G, Nie L, Kong T, Lei A. Nat. Commun. 2019; 10: 5467
    PubMed
  • 80 Morofuji T, Shimizu A, Yoshida J.-i. J. Am. Chem. Soc. 2014; 136: 4496
    PubMed
  • 81 Wu Y.-C, Jiang S.-S, Song R.-J, Li J.-H. Chem. Commun. (Cambridge) 2019; 55: 4371
    PubMed
  • 82 Weinberg NL, Weinberg HR. Chem. Rev. 1968; 68: 449
  • 83 Weinberg NL, Belleau B. Tetrahedron 1973; 29: 279
  • 84 Sauermann N, Meyer TH, Tian C, Ackermann L. J. Am. Chem. Soc. 2017; 139: 18452
    PubMed
  • 85 Li Y.-Q, Yang Q.-L, Fang P, Mei T.-S, Zhang D. Org. Lett. 2017; 19: 2905
    PubMed
  • 86 Shrestha A, Lee M, Dunn AL, Sanford MS. Org. Lett. 2018; 20: 204
    PubMed
  • 87 Tian C, Dhawa U, Struwe J, Ackermann L. Chin. J. Chem. 2019; 37: 552
  • 88 Fujimoto K, Tokuda Y, Maekawa H, Matsubara Y, Mizuno T, Nishiguchi I. Tetrahedron 1996; 52: 3889
  • 89 Hammerich O, Parker VD. Sulfur Rep. 1981; 1: 317
  • 90 Matsumoto K, Kozuki Y, Ashikari Y, Suga S, Kashimura S, Yoshida J.-i. Tetrahedron Lett. 2012; 53: 1916
  • 91 Zeng C.-C, Liu F.-J, Ping D.-W, Hu L.-M, Cai Y.-L, Zhong R.-G. Tetrahedron 2009; 65: 4505
  • 92 Zeng C.-C, Ping D.-W, Zhang S.-C, Zhong R.-G, Becker JY. J. Electroanal. Chem. 2008; 622: 90
  • 93 Fakhari AR, Hosseiny Davarani SS, Ahmar H, Hasheminasab K, Khavasi HR. J. Heterocycl. Chem. 2009; 46: 443
  • 94 Nematollahi D, Tammari E. J. Org. Chem. 2005; 70: 7769
    PubMed
  • 95 Fotouhi L, Nikoofar K. Tetrahedron Lett. 2013; 54: 2903
  • 96 Gitkis A, Becker JY. Electrochim. Acta 2010; 55: 5854
  • 97 Nematollahi D, Amani A. J. Electroanal. Chem. 2011; 651: 72
  • 98 Nematollahi D, Esmaili R. Tetrahedron Lett. 2010; 51: 4862
  • 99 Blum SP, Schollmeyer D, Turks M, Waldvogel SR. Chem.–Eur. J. 2020; 26: 8358
    PubMed
  • 100 Blum SP, Karakaya T, Schollmeyer D, Klapars A, Waldvogel SR. Angew. Chem. 2021; 133: 5114 Angew. Chem. Int. Ed. 2021; 60: 5056
    PubMed
  • 101 Wang Y, Tian B, Ding M, Shi Z. Chem.–Eur. J. 2020; 26: 4297
    PubMed
  • 102 Zhang L, Zhang Z, Hong J, Yu J, Zhang J, Mo F. J. Org. Chem. 2018; 83: 3200
    PubMed
  • 103 Hou Z.-W, Mao Z.-Y, Zhao H.-B, Melcamu YY, Lu X, Song J, Xu H.-C. Angew. Chem. 2016; 128: 9314 Angew. Chem. Int. Ed. 2016; 55: 9168
    PubMed
  • 104 Maity A, Frey BL, Hoskinson ND, Powers DC. J. Am. Chem. Soc. 2020; 142: 4990
    PubMed
  • 105 Kehl A, Schupp N, Breising VM, Schollmeyer D, Waldvogel SR. Chem.–Eur. J. 2020; 26: 15847
    PubMed
  • 106 Zhao H.-B, Hou Z.-W, Liu Z.-J, Zhou Z.-F, Song J, Xu H.-C. Angew. Chem. 2017; 129: 602 Angew. Chem. Int. Ed. 2017; 56: 587
    PubMed
  • 107 Gieshoff T, Kehl A, Schollmeyer D, Moeller KD, Waldvogel SR. Chem. Commun. (Cambridge) 2017; 53: 2974
    PubMed
  • 108 Qian X.-Y, Li S.-Q, Song J, Xu H.-C. ACS Catal. 2017; 7: 2730
  • 109 Wesenberg LJ, Herold S, Shimizu A, Yoshida J.-i, Waldvogel SR. Chem.–Eur. J. 2017; 23: 12096
    PubMed
  • 110 Kehl A, Breising VM, Schollmeyer D, Waldvogel SR. Chem.–Eur. J. 2018; 24: 17230
    PubMed