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DOI: 10.1055/s-0041-1738456
Synthesis of Aryl Carboxylic Acids through Ambient Electro-oxidation of Arylacetylenes
The authors gratefully acknowledge the financial support from the Start-up Fund from Nanjing Tech University (Grant Nos. 39837126).

Abstract
An efficient and environment-friendly synthesis of aryl carboxylic acids through the ambient electro-oxidation of the arylacetylenes is demonstrated. The reaction proceeds smoothly at certain applied potentials in a mixed solution of acetonitrile and water with potassium peroxymonosulfate (Oxone) as the additive. The isolated yields of the desired products are good up to 90%, and the reaction exhibits excellent functional-group tolerance. In this electrochemical system, transition metal catalysts, extra acids/bases, and high temperature are not required. This method may open up a pathway for the synthesis of carboxylic acids by the electrochemistry strategy.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1738456.
- Supporting Information
Publication History
Received: 21 July 2023
Accepted after revision: 05 September 2023
Article published online:
18 October 2023
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References
- 1a Cao HQ, Li JK, Zhang FG, Cahard D, Ma JA. Adv. Synth. Catal. 2020; 363: 688
- 1b Feng S, Buchwald SL. J. Am. Chem. Soc. 2021; 143: 4935
- 1c Vakarov SA, Gruzdev DA, Levit GL, Krasnov VP, Charushin VN, Chupakhin ON. Russ. Chem. Rev. 2019; 88: 1063
- 2 Wang X, Wang F, Huang F, Ni C, Hu J. Org. Lett. 2021; 23: 1764
- 3a Shirase S, Tamaki S, Shinohara K, Hirosawa K, Tsurugi H, Satoh T, Mashima K. J. Am. Chem. Soc. 2020; 142: 5668
- 3b Wu Y, Zhang M, Zhang Y, Li M, Feng W, Zheng X, Tang L. Org. Chem. Front. 2020; 7: 2719
- 4a Nguyen VT, Haug GC, Nguyen VD, Vuong NT. H, Arman HD, Larionov OV. Chem. Sci. 2021; 12: 6429
- 4b Miao Y.-Q, Kang J.-X, Ma Y.-N, Chen X. Green Chem. 2021; 23: 3595
- 5a Aleku GA, Roberts GW, Leys D. Green Chem. 2020; 22: 3927
- 5b Khan SN, Zaman MK, Li R. J. Org. Chem. 2020; 85: 5019
- 5c Sun Z. J. Org. Chem. 2020; 85: 5019
- 6a Juhl M, Laursen SL. R, Huang Y, Nielsen DU, Daasbjerg K, Skrydstrup T. ACS Catal. 2017; 7: 1392
- 6b Yamamoto Y, Ota M, Kodama S, Michimoto K, Nomoto A, Ogawa A, Furuya M, Kawakami K. ACS Omega 2021; 6: 2239
- 6c Siddiki SM. A. H, Rashed MN, Touchy AS, Jamil MA. R, Jing Y, Toyao T, Maeno Z, Shimizu K.-i. Catal. Sci. Technol. 2021; 11: 1949
- 6d Wang Y, Wu Z, Yu H, Han S, Wei Y. Green Chem. 2020; 22: 3150
- 6e Li C, Zhao P, Li R, Zhang B, Zhao W. Angew. Chem. Int. Ed. 2020; 59: 10913
- 6f Wang Y, Jiang X, Wang B. Chem. Commun. 2020; 56: 14416
- 6g Shi JB, Bu Q, Liu BY, Dai B, Liu N. J. Org. Chem. 2021; 86: 1850
- 7 Kolle S, Batra S. Org. Biomol. Chem. 2016; 14: 11048
- 8a Kumar VA, Reddy VP, Sridhar R, Srinivas B, Rao KR. Synlett 2009; 739
- 8b Ho CM, Yu WY, Che CM. Angew. Chem. Int. Ed. 2004; 43: 3303
- 9a Samanta S, Adak L, Jana R, Mostafa G, Tuononen HM, Ranu BC, Goswami S. Inorg. Chem. 2008; 47: 11062
- 9b Lee K, Kim YH, Han SB, Kang HK, Park S, Seo WS, Park JT, Kim B, Chang SB. J. Am. Chem. Soc. 2003; 125: 6844
- 10 Ranu BC, Bhadra S, Adak L. Tetrahedron Lett. 2008; 49: 2588
- 11a Shaikh TM, Hong F.-E. Adv. Synth. Catal. 2011; 353: 1491
- 11b Enthaler S. ChemCatChem 2011; 3: 1929
- 12 Rihter B, Masnovi J. J. Chem. Soc., Chem. Commun. 1988; 35
- 13 Srivastava S, Ali A, Tyagi A, Gupta R. Eur. J. Inorg. Chem. 2014; 2113
- 14 Urgoitia G, SanMartin R, Herrero MT, Dominguez E. Chem. Commun. 2015; 51: 4799
- 15 Miyamoto K, Sei Y, Yamaguchi K, Ochiai M. J. Am. Chem. Soc. 2009; 131: 1382
- 16 Sawant S, Aravinda Kumar K, Venkateswarlu V, Vishwakarma R. Synthesis 2015; 47: 3161
- 17a Capaldo L, Quadri LL, Ravelli D. Angew. Chem. Int. Ed. 2019; 58: 17508
- 17b Liu J, Lu L, Wood D, Lin S. ACS Cent. Sci. 2020; 6: 1317
- 18 Itoh A, Yamaguchi T, Nobuta T, Kudo Y, Hirashima S.-i, Tada N, Miura T. Synlett 2013; 24: 607
- 19 Feng Q, Wang Y, Zheng B, Huang S. Org. Lett. 2023; 25: 293