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Synthesis 2024; 56(16): 2507-2512
DOI: 10.1055/a-2309-6737
DOI: 10.1055/a-2309-6737
paper
Special Issue Flow Chemistry
Sequential Paired Electrochemical Transformation of Styrene Oxide via Anodic Meinwald Rearrangement and Cathodic Nitromethylation in an Electrochemical Flow Reactor with Catalytic Electrical Input
This work was supported by JSPS KAKENHI (Grant Nos. 22K05115 (S.S.), 22H02122 (K.M.), and 23K13748 (E.S.)) and the Ministry of Education, Culture, Sports, Science & Technology of Japan through Transformative Research Areas (A) 21A202 Digitalization-driven Transformative Organic Synthesis (Digi-TOS).
Abstract
Paired electrosynthesis, which utilize both anodic and cathodic events in electrolysis, enables attractive transformations with higher current efficiency than conventional electrosynthesis. The electrochemical flow technique has been widely employed to ensure stable reaction conditions and mitigate issues stemming from mass transfer. In this study, the electrochemical Meinwald rearrangement of styrene oxides was investigated, yielding aldehydes as intermediates, followed by the nitromethylation of aldehydes to produce β-nitro alcohols. These reactions were achieved with catalytic electrical input, enabling the conversion of various styrene oxides into the corresponding β-nitro alcohols.
Key words
electrochemical organic synthesis - paired electrolysis - Meinwald rearrangement - nitromethylation - flow synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2309-6737.
- Supporting Information
Publication History
Received: 05 April 2024
Accepted after revision: 19 April 2024
Accepted Manuscript online:
19 April 2024
Article published online:
06 May 2024
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References
- 1a Yan M, Kawamata Y, Baran PS. Chem. Rev. 2017; 117: 13230
- 1b Kärkäs MD. Chem. Soc. Rev. 2018; 47: 5786
- 1c Wiebe A, Gieshoff T, Möhle S, Rodrigo E, Zirbes M, Waldvogel SR. Angew. Chem. Int. Ed. 2018; 57: 5594
- 1d Möhle S, Zirbes M, Rodorigo E, Gieshoff T, Wiebe A, Waldvogel SR. Angew. Chem. Int. Ed. 2018; 57: 6018
- 1e Liang S, Xu K, Zeng C.-C, Tian H.-Y, Sun B.-G. Adv. Synth. Catal. 2018; 360: 4266
- 2a Li W, Nonaka T, Chou T.-C. Electrochemistry 1999; 67: 4
- 2b Marken F, Cresswell AJ, Bull SD. Chem. Rec. 2021; 21: 2585
- 2c Wu T, Moeller KD. Angew. Chem. Int. Ed. 2021; 60: 12883
- 3 Baizer MM, Hallvher RC. J. Electrochem. Soc. 1976; 123: 809
- 4 Hilt G. Angew. Chem. Int. Ed. 2003; 42: 1720
- 5 Hartmer M, Waldvogel SR. Chem. Commun. 2015; 51: 16346
- 6a Sattler LE, Otten CJ, Hilt G. Chem. Eur. J. 2020; 26: 3129
- 6b Rodrigo S, Um C, Mixdorf JC, Gunasekera D, Nguyen HM, Luo L. Org. Lett. 2020; 22: 6719
- 7a Watt K, Baker A, Wirth T. J. Flow Chem. 2014; 4: 2
- 7b Suga S, Okajima M, Fujiwara K, Yoshida J. J. Am. Chem. Soc. 2001; 123: 7941
- 7c Green RA, Brown RC. D, Pletcher D, Harji B. Org. Process Res. Dev. 2015; 19: 1424
- 7d Gütz C, Stenglein A, Waldvogel SR. Org. Process Res. Dev. 2017; 21: 771
- 7e Wang D, Wang P, Wang S, Chen Y.-H, Zhang H, Lei A. Nat. Commun. 2019; 10: 2796
- 7f Laudadio G, Barmpoutsis E, Schotten C, Struik L, Govaerts S, Browne DL, Noël T. J. Am. Chem. Soc. 2019; 141: 5664
- 7g Zhong X, Hoque MA, Graaf MD, Harper KC, Wang F, Genders JD, Stahl SS. Org. Process Res. Dev. 2021; 25: 2601
- 8a Pintauro PN, Johnson DK, Park K, Baizer MM, Nobe K. J. Appl. Electrochem. 1984; 14: 209
- 8b Suga S, Okajima M, Fujiwara K, Yoshida J. QSAR Comb. Sci. 2005; 24: 728
- 8c Amemiya F, Kashiwagi T, Fuchigami T, Atobe M. Chem. Lett. 2011; 40: 606
- 8d Kashiwagi T, Fuchigami T, Saito T, Nishiyama S, Atobe M. Chem. Lett. 2014; 43: 799
- 8e Tanaka K, Yoshizawa H, Atobe M. Synlett 2019; 30: 1194
- 8f Mo Y, Lu Z, Rughoobur G, Patil P, Gershenfeld N, Akinwande AI, Buchwald SL, Jensen KF. Science 2020; 368: 1352
- 8g Cao Y, Knijff J, Delparish A, d’Angelo MF. N, Noël T. ChemSusChem 2021; 14: 590
- 9a Sato E, Fujii M, Tanaka H, Mitsudo K, Kondo M, Takizawa S, Sasai H, Washio T, Ishikawa K, Suga S. J. Org. Chem. 2021; 86: 16035
- 9b Sato E, Tachiwaki G, Fujii M, Mitsudo K, Washio T, Takizawa S, Suga S. Org. Process Res. Dev. 2023; 27 in press, DOI: DOI: 10.1021/acs.oprd.2c00267.
- 10 Sato E, Fujii M, Mitsudo K, Suga S. ChemElectroChem 2023; 11: e202300499
- 11 Uneyama K, Ishimura A, Fujii K, Torii S. Tetrahedron Lett. 1983; 24: 2857
- 12a House HO. J. Am. Chem. Soc. 1955; 77: 3070
- 12b Meinwald J, Labana SS, Chadha MS. J. Am. Chem. Soc. 1963; 85: 582
- 13 Elinson MN, Ilovaisky AI, Merkulova VM, Barba F, Batanero B. Tetrahedron 2008; 64: 5915
- 14 Homma H, Hasegawa R, Yokoyama T, Tajima T. Electrochemistry 2023; 91: 112008
- 15 Uneyama K. J. Synth. Org. Chem. Jpn. 1985; 43: 557
- 16 Tse MK, Klawonn M, Bhor S, Dolbler C, Anilkumar G, Hugl H, Magerlein W, Beller M. Org. Lett. 2005; 7: 987
- 17 Keutz TV, Cantillo D, Kappe CO. Org. Lett. 2020; 22: 7537
- 18 Kang B, Kim M, Lee J, Do Y, Chang S. J. Org. Chem. 2006; 71: 6721
- 19 Sharma S, Kumar M, Bhatt V, Nayal OS, Thakur MS, Kumar N, Singh BS. Tetrahedron Lett. 2016; 57: 5003
For selected examples of electorochemical flow synthesis, see: