Synthesis, Table of Contents Synthesis DOI: 10.1055/a-2518-0987 paper Bürgenstock Special Section 2023 – Future Stars in Organic Chemistry EDA Complexation of Two Donor Molecules Initiating Radical Cation Cyclizations Julian C. G. Kürschner‡ , Martin Utikal‡ , Lena Lezius , Rubaishan Jeyaseelan , Line Næsborg ∗ Recommend Article Abstract Buy Article All articles of this category Abstract In this study, a catalyst-free EDA complexation of two donor molecules using an acidic solvent is presented. The electron-rich aromatic compound (E)-anethole is slowly protonated by the solvent hexafluoroisopropanol (HFIP), leading to the rapid formation of a photoactive EDA complex between a protonated (E)-anethole and another (E)-anethole molecule. This resulting EDA complex initiates radical chain cyclization reactions under green light irradiation. Key words Key wordsEDA complex - radical cyclization - catalyst free - photochemistry Full Text References References 1 Mulliken RS. J. Am. Chem. Soc. 1952; 74: 811 2 Mulliken RS. J. Am. Chem. Soc. 1950; 72: 600 3 Crisenza GE. M, Mazzarella D, Melchiorre P. J. Am. Chem. Soc. 2020; 142: 5461 4 Tobisu M, Furukawa T, Chatani N. Chem. Lett. 2013; 42: 1203 5 Arceo E, Jurberg ID, Álvarez-Fernández A, Melchiorre P. Nat. Chem. 2013; 5: 750 6 Lima CG. S, de M Lima T, Duarte M, Jurberg ID, Paixão MW. ACS Catal. 2016; 6: 1389 7 Rosokha SV, Kochi JK. Acc. Chem. Res. 2008; 41: 641 8 Tasnim T, Ayodele MJ, Pitre SP. J. Org. Chem. 2022; 87: 10555 9 Bosque I, Bach T. ACS Catal. 2019; 9: 9103 10 Xue T, Ma C, Liu L, Xiao C, Ni S.-F, Zeng R. Nat. Commun. 2024; 15: 1455 11 Paut J, Baldon S, Anselmi E, Dell’Amico L, Dagousset G, Magnier E. Adv. Synth. Catal. 2024; 366: 3500 12 Jeyaseelan R, Liu W, Zumbusch J, Næsborg L. Green Chem. 2025; 13 Morack T, Mück-Lichtenfeld C, Gilmour R. Angew. Chem. Int. Ed. 2019; 58: 1208 14 Woźniak Ł, Murphy JJ, Melchiorre P. J. Am. Chem. Soc. 2015; 137: 5678 15 Cuadros S, Rosso C, Barison G, Costa P, Kurbasic M, Bonchio M, Prato M, Filippini G, Dell’Amico L. Org. Lett. 2022; 24: 2961 16 Lasky MR, Salvador TK, Mukhopadhyay S, Remy MS, Vaid TP, Sanford MS. Angew. Chem. Int. Ed. 2022; 61: e202208741 17 Huang P, Lv C, Song H, Wang C, Du J, Li J, Sun B, Jin C. Green Chem. 2024; 26: 7198 18 Bargon J, Gardini GP. Tetrahedron Lett. 1976; 2993 19 Ramos-Villaseñor JM, Rodríguez-Cárdenas E, Barrera Díaz CE, Frontana-Uribe BA. J. Electrochem. Soc. 2020; 167: 155509 20 Wang S, Force G, Guillot R, Carpentier J.-F, Sarazin Y, Bour C, Gandon V, Lebœuf D. ACS Catal. 2020; 10: 10794 21 Shida N, Imada Y, Nagahara S, Okada Y, Chiba K. Chem. Commun. 2019; 24 22 Colomer I, Chamberlain AE. R, Haughey MB, Donohoe TJ. Nat. Rev. Chem. 2017; 1: 1 23 Bégué J.-P, Bonnet-Delpon D, Crousse B. Synlett 2004; 18 24 Entgelmeier L, Mori S, Sendo S, Yamaguchi R, Suzuki R, Yanai T, García Mancheño O, Ohmatsu K, Ooi T. Angew. Chem. Int. Ed. 2024; 63: e202404890 25 Ni Y, Lebelt J, Barp M, Kreuter F, Buttkus H, Jin J, Kretzschmar M, Tonner-Zech R, Asmis KR, Gulder T. Angew. Chem. Int. Ed. 2024; 63: e202417889 26 Arnold AM, Dullinger P, Biswas A, Jandl C, Horinek D, Gulder T. Nat. Commun. 2023; 14: 813 27 Piejko M, Moran J, Lebœuf D. ACS Org. Inorg. Au 2024; 4: 287 28 Motiwala HF, Armaly AM, Cacioppo JG, Coombs TC, Koehn KR. K, Norwood VM, Aubé J. Chem. Rev. 2022; 122: 12544 29 Colomer I, Batchelor-McAuley C, Odell B, Donohoe TJ, Compton RG. J. Am. Chem. Soc. 2016; 138: 8855 30 Colomer I. ACS Catal. 2020; 10: 6023 31 Kuznetsov DM, Tumanov VV, Smit WA. J. Polym. Res. 2013; 20: 128 32 Luo M.-J, Xiao Q, Li J.-H. Chem. Soc. Rev. 2022; 51: 7206 33 Lin S, Ischay MA, Fry CG, Yoon TP. J. Am. Chem. Soc. 2011; 133: 19350 34 Tanaka K, Kishimoto M, Sukekawa M, Hoshino Y, Honda K. Tetrahedron Lett. 2018; 59: 3361 35 Nagahara S, Wakamatsu H, Okada Y, Chiba K. Eur. J. Org. Chem. 2018; 6720 36 Spicer RL, Stergiou AD, Young TA, Duarte F, Symes MD, Lusby PJ. J. Am. Chem. Soc. 2020; 142: 2134 37 Yu Y, Fu Y, Zhong F. Green Chem. 2018; 20: 1743 38 Colomer I, Coura Barcelos R, Donohoe TJ. Angew. Chem. Int. Ed. 2016; 55: 4748 39 Zhao Y, Antonietti M. Angew. Chem. Int. Ed. 2017; 56: 9336 40 Zhang XS, Paton R. Chem. Sci. 2020; 11: 9309 41 Lee AA, Swierk JR. J. Am. Chem. Soc. 2024; 146; 34900 42 Wortman AK, Stephenson CR. J. Chem 2023; 9: 2390 43 Liu Z, Wang S, Liu Z, Ding Y, Hu Y, Liu R, Zhang Z, Qiu Y.-F, Lei J. Org. Biomol. Chem. 2024; 22: 7834 44 Farney EP, Chapman SJ, Swords WB, Torelli MD, Hamers RJ, Yoon TP. J. Am. Chem. Soc. 2019; 141: 6385 45 Nakayama K, Maeta N, Horiguchi G, Kamiya H, Okada Y. Org. Lett. 2019; 21: 2246 46 Kollmann J, Zhang Y, Schilling W, Zhang T, Riemer D, Das S. Green Chem. 2019; 21: 1916 47 Tanaka K, Iwama Y, Kishimoto M, Ohtsuka N, Hoshino Y, Honda K. Org. Lett. 2020; 22: 5207 48 Rybicka-Jasińska K, Szeptuch Z, Kubiszewski H, Kowaluk A. Org. Lett. 2023; 25: 1142 49 Horibe T, Ohmura S, Ishihara K. J. Am. Chem. Soc. 2019; 141: 1877 Supplementary Material Supplementary Material Supporting Information
