Synthesis, Table of Contents Synthesis 2023; 55(18): 2985-2992DOI: 10.1055/a-2038-9146 paper Special Issue Electrochemical Organic Synthesis Electrosynthesis of Flavanones via oxa-Michael Addition Using Sacrificial Electrodes Authors Author Affiliations William A. B. Santos a Department of Chemistry, State University of Santa Catarina (UDESC), Joinville – SC, 89219-719, Brazil b Department of Chemistry, Federal University of Santa Catarina (UFSC), Florianópolis – SC, 88040-900, Brazil Pedro P. de Castro c Department of Chemistry, Federal University of São Carlos (UFSCar), São Carlos – SP, 13565-905, Brazil Fernando R. Xavier a Department of Chemistry, State University of Santa Catarina (UDESC), Joinville – SC, 89219-719, Brazil Antonio L. Braga b Department of Chemistry, Federal University of Santa Catarina (UFSC), Florianópolis – SC, 88040-900, Brazil Guilherme M. Martins∗ c Department of Chemistry, Federal University of São Carlos (UFSCar), São Carlos – SP, 13565-905, Brazil Samuel R. Mendes ∗ a Department of Chemistry, State University of Santa Catarina (UDESC), Joinville – SC, 89219-719, Brazil Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract An electrochemical synthesis of flavanones via oxa-Michael addition using silver electrode as a sacrifice is reported. This electrosynthetic system showed good yields, broad substrate scope, and good functional group tolerance. Additionally, the method proved to be applicable on a gram-scale. Several studies were carried out to elucidate the reaction mechanism, such as control reactions, cyclic voltammetry, and theoretical studies, allowing the proposal of a plausible pathway for this transformation. Key words Key wordselectrosynthesis - sacrificial electrodes - silver - flavonoids - cyclization Full Text References References 1 Addi M, Elbouzidi A, Abid M, Tungmunnithum D, Elamrani A, Hano C. Appl. Sci. 2021; 12: 29 2 Kumar D, Ladaniya MS, Gurjar M, Kumar S. Sci. Rep. 2022; 12: 6684 3 Gleńsk M, Dudek MK, Ciach M, Włodarczyk M. Nat. Prod. Res. 2021; 35: 1474 4 Obaid RJ, Mughal EU, Naeem N, Sadiq A, Alsantali RI, Jassas RS, Moussa Z, Ahmed SA. RSC Adv. 2021; 11: 22159 5 Cabrera M, Simoens M, Falchi G, Lavaggi ML, Piro OE, Castellano EE, Vidal A, Azqueta A, Monge A, de Ceráin AL, Sagrera G, Seoane G, Cerecetto H, González M. Bioorg. Med. Chem. 2007; 15: 3356 6 Wang X, Cao Y, Chen S, Lin J, Bian J, Huang D. J. Agric. Food Chem. 2021; 69: 7285 7 Albuquerque de Oliveira Mendes L, Ponciano CS, Depieri Cataneo AH, Wowk PF, Bordignon J, Silva H, Vieira de Almeida M, Ávila EP. Chem. Biol. Interact. 2020; 331: 109218 8 Lowe HI. C, Toyang NJ, Watson CT, Ayeah KN, Bryant J. Cancer Cell Int. 2017; 17: 38 9 Tutunchi H, Naeini F, Ostadrahimi A, Hosseinzadeh-Attar MJ. Phyther. Res. 2020; 34: 3137 10 Gour A, Manhas D, Bag S, Gorain B, Nandi U. Phyther. Res. 2021; 35: 4258 11 Alzaabi MM, Hamdy R, Ashmawy NS, Hamoda AM, Alkhayat F, Khademi NN, Al Joud SM. A, El-Keblawy AA, Soliman SS. M. Phytochem. Rev. 2022; 21: 291 12 Jannat K, Paul AK, Bondhon TA, Hasan A, Nawaz M, Jahan R, Mahboob T, Nissapatorn V, Wilairatana P, Pereira M. deL, Rahmatullah M. Pharmaceutics 2021; 13: 1895 13 Majed Z, Said S, Shareef O. Egypt. J. Chem. 2020; 63: 4379 14 Miura M, Shigematsu K, Toriyama M, Motohashi S. Tetrahedron Lett. 2021; 85: 153480 15 Mondal R, Das Gupta A, Mallik AK. Tetrahedron Lett. 2011; 52: 5020 16 Nawghare BR, Gaikwad SV, Raheem A, Lokhande PD. J. Chil. Chem. Soc. 2014; 59: 2284 17 Desai VG, Desai SR. Curr. Org. Synth. 2018; 14: 1180 18 Yuan Y, Lei A. Nat. Commun. 2020; 11: 802 19 Lam K, Dobbs A, Leech MC, Petti A, Garcia AD. React. Chem. Eng. 2020; 5: 977 20 Gomollón-Bel F. Chem. Int. 2021; 43: 13 21 Ley SV, Baxendale IR. Nat. Rev. Drug Discov. 2002; 1: 573 22 Martins GM, Magalhães MF. A, Brocksom TJ, Bagnato VS, de Oliveira KT. J. Flow. Chem. 2022; 12: 371 23 Kar S, Sanderson H, Roy K, Benfenati E, Leszczynski J. Chem. Rev. 2022; 122: 3637 24 Schaub T. Chem. Eur. J. 2021; 27: 1865 25 Tanbouza N, Ollevier T, Lam K. iScience 2020; 23: 101720 26 Leech MC, Garcia AD, Petti A, Dobbs AP, Lam K. React. Chem. Eng. 2020; 5: 977 27 Sequeira CA. C, Santos DM. F. J. Braz. Chem. Soc. 2009; 20: 387 28 Cardoso DS. P, Šljukić B, Santos DM. F, Sequeira CA. C. Org. Process Res. Dev. 2017; 21: 1213 29 Goodenough JB. Energy Environ. Sci. 2014; 7: 14 30 Chen K, Xue D. J. Mater. Chem. A 2016; 4: 7522 31 Feng Y, Yang L, Liu J, Logan BE. Environ. Sci. Water Res. Technol. 2016; 2: 800 32 Shatskiy A, Lundberg H, Kärkäs MD. ChemElectroChem 2019; 6: 4067 33 Sbei N, Hardwick T, Ahmed N. ACS Sustain. Chem. Eng. 2021; 9: 6148 34 Heard DM, Lennox AJ. J. Angew. Chem. Int. Ed. 2020; 59: 18866 35 Bijaya BK, Pokhrel T, Shrestha D, Adhikari A, Shirinfar B, Ahmed N. In Reference Module in Chemistry, Molecular Sciences and Chemical Engineering . Elsevier; Amsterdam: 2023. 36 Mitsudo K, Shiraga T, Mizukawa J, Suga S, Tanaka H. Chem. Commun. 2010; 46: 9256 37 Seavill PW, Holt KB, Wilden JD. RSC Adv. 2019; 9: 29300 38 Seavill PW, Holt KB, Wilden JD. Green Chem. 2018; 20: 5474 39 Chapman MR, Shafi YM, Kapur N, Nguyen BN, Willans CE. Chem. Commun. 2015; 51: 1282 40 Peters BK, Rodriguez KX, Reisberg SH, Beil SB, Hickey DP, Kawamata Y, Collins M, Starr J, Chen L, Udyavara S, Klunder K, Gorey TJ, Anderson SL, Neurock M, Minteer SD, Baran PS. Science 2019; 363: 838 41 Manabe S, Wong CM, Sevov CS. J. Am. Chem. Soc. 2020; 142: 3024 42 De Baere K, Verstraelen H, Lemmens L, Lenaerts S, Dewil R, Van Ingelgem Y, Potters G. J. Mar. Sci. Technol. 2014; 19: 116 43 Xu L, Xin Y, Ma L, Zhang H, Lin Z, Li X. Corros. Commun. 2021; 2: 33 44 Zayed A, Garbatov Y, Guedes Soares C. Ocean Eng. 2018; 163: 299 45 Martins GM, Zimmer GC, Mendes SR, Ahmed N. Green Chem. 2020; 22: 4849 46 Martins GM, Shirinfar B, Hardwick T, Ahmed N. ChemElectroChem 2019; 6: 1300 47 Meirinho AG, Pereira VF, Martins GM, Saba S, Rafique J, Braga AL, Mendes SR. Eur. J. Org. Chem. 2019; 6423 48 Scheide MR, Schneider AR, Jardim GA. M, Martins GM, Durigon DC, Saba S, Rafique J, Braga AL. Org. Biomol. Chem. 2020; 18: 4916 49 Doerner CV, Scheide MR, Nicoleti CR, Durigon DC, Idiarte VD, Sousa MJ. A, Mendes SR, Saba S, Neto JS. S, Martins GM, Rafique J, Braga AL. Front. Chem. 2022; 10: 880099 50 Lazzaris MJ, Martins GM, Xavier FR, Braga AL, Mendes SR. Eur. J. Org. Chem. 2021; 4411 51 Scheide MR, Nicoleti CR, Martins GM, Braga AL. Org. Biomol. Chem. 2021; 19: 2578 52 Sbei N, Martins GM, Shirinfar B, Ahmed N. Chem. Rec. 2020; 20: 1530 53 Martins GM, Sbei N, Zimmer GC, Ahmed N. IntechOpen. 2021 , C-H Activation/Functionalization via Metalla-Electrocatalysis. Electrocatalysis and Electrocatalysts for a Cleaner Environment - Fundamentals and Applications. DOI: 54 Benbouguerra N, Richard T, Saucier C, Garcia F. Antioxidants 2020; 9: 800 55 Mahanty K, Halder A, Maiti D, De Sarkar S. Synthesis 2023; 55: 400 56 Yang J, Lai J, Kong W, Li S. J. Agric. Food Chem. 2022; 70: 3409 57 Bera SK, Maharana RR, Samanta K, Mal P. Org. Biomol. Chem. 2022; 20: 7085 58 Han F, Choi PH, Ye C.-X, Grell Y, Xie X, Ivlev SI, Chen S, Meggers E. ACS Catal. 2022; 12: 10304 59 Jiang H, Zheng X, Yin Z, Xie J. J. Chem. Res. 2011; 35: 220 60 Dauzonne D, Monneret C. Synthesis 1997; 1305 61 Pawlak A, Henklewska M, Hernández Suárez B, Łużny M, Kozłowska E, Obmińska-Mrukowicz B, Janeczko T. Molecules 2020; 25: 4362 62 Carvalho MH. R, Ribeiro JP. R. S, De Castro PP, Passos ST. A, Neto BA. D, Dos Santos HF, Amarante GW. J. Org. Chem. 2022; 87: 11007 63 Santos IA, de Castro PP, Dos Santos HF, Amarante GW. Eur. J. Org. Chem. 2022; e202200287 Supplementary Material Supplementary Material Supporting Information (PDF) (opens in new window)
