Solvent Control in Electro-Organic Synthesis

Lara Schulz; Siegfried R. Waldvogel

doi:10.1055/s-0037-1610303

Synlett, Inhaltsverzeichnis

CC BY ND NC 4.0 · Synlett 2019; 30(03): 275-286
DOI: 10.1055/s-0037-1610303

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Solvent Control in Electro-Organic Synthesis

Authors

Lara Schulz
Siegfried R. Waldvogel *

Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10–14, 55128 Mainz, Germany eMail: waldvogel@uni-mainz.de

Abstract

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Abstract

Exploiting the solvent control within electro-organic conversions is a far underestimated parameter in prep-scale electrolysis. The beneficial application in several transformations is outlined and in particular discussed for the dehydrogenative coupling of arenes and heteroarenes. This simple electrolytic strategy in fluorinated solvents allows the modulation of the substrate’s nucleophilicity and the stabilization of the intermediates as well as of the final product from over-oxidation.

1 Introduction

2 Solvent Effects in Kolbe Electrolysis and Anodic Fluorination

3 Unique Solvent Effects of 1,1,1,3,3,3-Hexafluoropropan-2-ol (HFIP)

4 Anodic Dehydrogenative Coupling Reactions with Use of HFIP as the Solvent

5 Conclusion

Key words

C–C coupling - electrochemical fluorination - electrosynthesis - Kolbe electrolysis - N–C coupling - solvent effect - 1,1,1,3,3,3-hexafluoropropan-2-ol

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Referenzen

References

1a Fuchigami T, Atobe M, Inagi S. Fundamentals and Applications of Organic Electrochemistry. Synthesis Materials Devices . John Wiley & Sons; Chichester: 2015
1b Möhle S, Zirbes M, Rodrigo E, Gieshoff T, Wiebe A, Waldvogel SR. Angew. Chem. Int. Ed. 2018; 57: 6018

2 Wiebe A, Gieshoff T, Möhle S, Rodrigo E, Zirbes M, Waldvogel SR. Angew. Chem. Int. Ed. 2018; 57: 5594
3 Grimshaw J. Electrochemical Reactions and Mechanisms in Organic Chemistry . Elsevier; Amsterdam and New York: 2000
4 Organic Electrochemistry . Hammerich O, Speiser B. CRC Press; Boca Raton: 2016

5a Chiba K, Kim S. Electrochemistry 2009; 77: 21
5b Shoji T, Haraya S, Kim S, Chiba K. Electrochim. Acta 2016; 200: 290

6 Heinze J, Steckhan E. Top. Curr. Chem . Springer; Berlin: 1990. Vol. 152
7 Fuchigami T, Inagi S. Chem. Commun. 2011; 47: 10211
8 Renaud RN, Sullivan DE. Can. J. Chem. 1973; 51: 772
9 Kimura K, Horie S, Minato I, Odaira Y. Chem. Lett. 1973; 2: 1209

10a Rozhkov IN. Russ. Chem. Rev. 1976; 45: 615
10b Laurent E, Marquet B, Tardivel R, Thiebault H. Tetrahedron Lett. 1987; 28: 2359

11a Meurs JH. H, Eilenberg W. Tetrahedron 1991; 47: 705
11b Lee SM, Roseman JM, Blair Zartman C, Morrison EP, Harrison SJ, Stankiewicz CA, Middleton WJ. J. Fluorine Chem. 1996; 77: 65
11c Suryanarayanan V, Noel M. J. Fluorine Chem. 1998; 92: 177

12 Hasegawa M, Ishii H, Fuchigami T. Green Chem. 2003; 5: 512

13a Eberson L, Hartshorn MP, Persson O. J. Chem. Soc., Chem. Commun. 1995; 1131
13b Eberson L, Persson O, Hartshorn MP. Angew. Chem. Int. Ed. 1995; 34: 2268

14 Hollóczki O, Berkessel A, Mars J, Mezger M, Wiebe A, Waldvogel SR, Kirchner B. ACS Catal. 2017; 7: 1846

15a Berkessel A, Adrio JA, Hüttenhain D, Neudörfl JM. J. Am. Chem. Soc. 2006; 128: 8421
15b Shuklov I, Dubrovina N, Börner A. Synthesis 2007; 2925

16 Berkessel A, Adrio JA. J. Am. Chem. Soc. 2006; 128: 13412
17 Kirste A, Nieger M, Malkowsky IM, Stecker F, Fischer A, Waldvogel SR. Chem. Eur. J. 2009; 15: 2273
18 Berkessel A, Vormittag SS, Schlörer NE, Neudörfl J.-M. J. Org. Chem. 2012; 77: 10145
19 Seebach D, Beck AK, Heckel A. Angew. Chem. Int. Ed. 2001; 40: 92
20 Wagner JP, Schreiner PR. Angew. Chem. Int. Ed. 2015; 54: 12274
21 Morofuji T, Shimizu A, Yoshida J.-i. Angew. Chem. Int. Ed. 2012; 51: 7259
22 Malkowsky IM, Rommel CE, Fröhlich R, Griesbach U, Pütter H, Waldvogel SR. Chem. Eur. J. 2006; 12: 7482

23a Malkowsky IM, Rommel CE, Wedeking K, Fröhlich R, Bergander K, Nieger M, Quaiser C, Griesbach U, Pütter H, Waldvogel SR. Eur. J. Org. Chem. 2006; 241
23b Barjau J, Königs P, Kataeva O, Waldvogel S. Synlett 2008; 2309
23c Barjau J, Schnakenburg G, Waldvogel SR. Angew. Chem. Int. Ed. 2011; 50: 1415

24 Malkowsky IM, Griesbach U, Pütter H, Waldvogel SR. Eur. J. Org. Chem. 2006; 4569

25a Montilla F, Michaud PA, Morallón E, Vázquez JL, Comninellis C. Electrochim. Acta 2002; 47: 3509
25b Morão A, Lopes A, Pessoa de Amorim MT, Gonçalves IC. Electrochim. Acta 2004; 49: 1587

26 Kirste A, Schnakenburg G, Waldvogel SR. Org. Lett. 2011; 13: 3126
27 Kirste A, Schnakenburg G, Stecker F, Fischer A, Waldvogel SR. Angew. Chem. Int. Ed. 2010; 49: 971
28 Francke R, Cericola D, Kötz R, Weingarth D, Waldvogel SR. Electrochim. Acta 2012; 62: 372
29 Colomer I, Chamberlain AE. R, Haughey MB, Donohoe TJ. Nat. Rev. Chem. 2017; 1: 88
30 Kirste A, Elsler B, Schnakenburg G, Waldvogel SR. J. Am. Chem. Soc. 2012; 134: 3571
31 Elsler B, Wiebe A, Schollmeyer D, Dyballa KM, Franke R, Waldvogel SR. Chem. Eur. J. 2015; 21: 12321
32 Wiebe A, Schollmeyer D, Dyballa KM, Franke R, Waldvogel SR. Angew. Chem. Int. Ed. 2016; 55: 11801
33 Wiebe A, Lips S, Schollmeyer D, Franke R, Waldvogel SR. Angew. Chem. Int. Ed. 2017; 56: 14727

Selection of patents submitted by Waldvogel et al.:

34a Dyballa KM, Franke R, Fridag D, Waldvogel SR, Elsler B. PCT Int. Appl. WO 2014135236 A1 20140912, Ger. Offen. 2014 DE 102013203865 A1 20140911, US Patent 9,879,353, 2014
34b Dyballa KM, Franke R, Fridag D, Waldvogel SR, Elsler B. PCT Int. Appl. WO 2014135405 A1 20140912, Ger. Offen. 2014 DE 102013203867 A1 20140911, 2014
34c Dyballa KM, Franke R, Fridag D, Waldvogel SR, Elsler B. PCT Int. Appl WO 2014135237 A1 20140912, Ger. Offen. DE 102013203866 A1 20140911, 2014
34d Dyballa KM, Franke R, Fridag D, Waldvogel SR, Elsler B, Enders M. PCT Int. Appl , WO 2016034332 A1 20160310, 2016
34e Dyballa KM, Franke R, Fridag D, Waldvogel SR, Elsler B, Enders M. PCT Int. Appl WO 2016034330 A1 20160310, 2016
34f Dyballa KM, Franke R, Fridag D, Waldvogel SR, Elsler B, Enders M. PCT Int. Appl WO 2016034327, 2016
34g Dyballa KM, Franke R, Fridag D, Waldvogel SR, Elsler B, Enders M. PCT Int. Appl WO 2016034328 A1 20160310, 2016
34h Dyballa KM, Franke R, Fridag D, Waldvogel SR, Elsler B, Wiebe A. Ger. Offen DE 102015207280 A1 20160303, 2016
34i Dyballa KM, Franke R, Fridag D, Waldvogel SR, Elsler B, Enders M. Ger. Offen. DE 102014217537 A1 20160303, 2016
34j Dyballa KM, Franke R, Fridag D, Waldvogel SR, Elsler B, Wiebe A. Eur. Pat. Appl EP 3133054 A1 20170222, 2017
34k Dyballa KM, Franke R, Fridag D, Waldvogel SR, Elsler B, Wiebe A. Ger. Offen DE 102015215995 A1 20170223, 2017
34l Dyballa KM, Franke R, Fridag D, Waldvogel SR, Elsler B, Wiebe A. Ger. Offen. DE 102015215997 A1 20170223, 2017
34m Dyballa KM, Franke R, Fridag D, Waldvogel SR, Elsler B, Wiebe A. Ger. Offen DE 102015215998 A1 20170223, 2017
34n Dyballa KM, Franke R, Fridag D, Waldvogel SR, Elsler B, Wiebe A, Lips S. Eur. Pat. Appl. EP 3133189 A1 20170222, 2017
34o Dyballa KM, Franke R, Fridag D, Dahms B, Waldvogel SR. Eur. Pat. Appl EP 3252033 A1 20171206, 2017
34p Waldvogel SR, Dahms B, Franke R. Eur. Pat. Appl. EP 17203772.3, 2018
34q Waldvogel SR, Frontana-Uribe BA, Wiebe A, Lips S, Franke R. Eur. Pat. Appl EP 17203773.1, 2018

35 Riehl B, Dyballa K, Franke R, Waldvogel S. Synthesis 2016; 49: 252
36 Schulz L, Enders M, Elsler B, Schollmeyer D, Dyballa KM, Franke R, Waldvogel SR. Angew. Chem. Int. Ed. 2017; 56: 4877
37 Schulz L, Franke R, Waldvogel SR. ChemElectroChem 2018; 5: 2069
38 Mohilner DM, Adams RN, Argersinger WJ. J. Am. Chem. Soc. 1962; 84: 3618
39 Elsler B, Schollmeyer D, Dyballa KM, Franke R, Waldvogel SR. Angew. Chem. Int. Ed. 2014; 53: 5210
40 Wiebe A, Riehl B, Lips S, Franke R, Waldvogel SR. Science Advances 2017; 3: eaao3920/1
41 Dahms B, Franke R, Waldvogel SR. ChemElectroChem 2018; 5: 1249
42 Lips S, Wiebe A, Elsler B, Schollmeyer D, Dyballa KM, Franke R, Waldvogel SR. Angew. Chem. Int. Ed. 2016; 55: 10872
43 Lips S, Frontana-Uribe BA, Dörr M, Schollmeyer D, Franke R, Waldvogel SR. Chem. Eur. J. 2018; 24: 6057
44 Lips S, Schollmeyer D, Franke R, Waldvogel SR. Angew. Chem. Int. Ed. 2018; 57: 13325
45 Imada Y, Röckl JL, Wiebe A, Gieshoff T, Schollmeyer D, Chiba K, Franke R, Waldvogel SR. Angew. Chem. Int. Ed. 2018; 57: 12136
46 Gieshoff T, Schollmeyer D, Waldvogel SR. Angew. Chem. Int. Ed. 2016; 55: 9437
47 Kehl A, Gieshoff T, Schollmeyer D, Waldvogel SR. Chem. Eur. J. 2018; 24: 590
48 Gieshoff T, Kehl A, Schollmeyer D, Moeller KD, Waldvogel SR. Chem. Commun. 2017; 53: 2974
49 Gieshoff T, Kehl A, Schollmeyer D, Moeller KD, Waldvogel SR. J. Am. Chem. Soc. 2017; 139: 12317