Synthesis, Table of Contents Synthesis 2025; 57(20): 3013-3021DOI: 10.1055/a-2640-5375 Paper Published as part of the Special Issue in Honor of Prof. Franziska Schoenebeck, the 2025 Women in Chemistry Award Winner Solar Light-Assisted C–H Activation and C–C Coupling of Hindered N, N-Dimethyl-Anilines with Activated Methylene Compounds Authors Author Affiliations Sourav Kumar Santra‡ 1 Department of Chemical Sciences, Ariel University, 40700000 Ariel, Israel (Ringgold ID: RIN42732) Jonatan Rahamim‡ 1 Department of Chemical Sciences, Ariel University, 40700000 Ariel, Israel (Ringgold ID: RIN42732) Ortal Dorfman 1 Department of Chemical Sciences, Ariel University, 40700000 Ariel, Israel (Ringgold ID: RIN42732) Abhijit Kashid 1 Department of Chemical Sciences, Ariel University, 40700000 Ariel, Israel (Ringgold ID: RIN42732) Galit Parvari 2 Schulich Faculty of Chemistry, Technion, Israel Institute of Technology, Haifa, Israel (Ringgold ID: RIN26747) Yoav Eichen 2 Schulich Faculty of Chemistry, Technion, Israel Institute of Technology, Haifa, Israel (Ringgold ID: RIN26747) Alex M. Szpilman 1 Department of Chemical Sciences, Ariel University, 40700000 Ariel, Israel (Ringgold ID: RIN42732) Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract This article describes the use of dimethyl-aniline-alkyl halide charge transfer complexes as a linchpin for sunlight-initiated C–C bond formation with activated methylene compounds, including malonates, malononitriles, and 2-cyano-esters. DFT calculations shed light on charge transfer complex formation and structure as well as on the mechanism. Keywords KeywordsSunlight - Visible light - Charge-transfer complex - Electron donor–acceptor complex - C–C bond formation Full Text References References 1 Prier CK, Rankic DA, MacMillan DWC. Chem Rev 2013; 113: 5322-5363 2a Staveness D, Bosque I, Stephenson CRJ. Acc Chem Res 2016; 49: 2295-2306 2b Romero NA, Nicewicz DA. Chem Rev 2016; 116: 10075-10166 2c Stephenson CRJ, Yoon T, MacMillan DWC. Visible Light Photocatalysis in Organic Chemistry. 2018 3a Freeman DB, Furst L, Condie AG, Stephenson CRJ. Org Lett 2012; 14: 94-97 3b Beatty JW, Stephenson CRJ. Acc Chem Res 2015; 48: 1474-1484 4 Lautenberger WJ, Jones EN, Miller JG. J Am Chem Soc 1968; 90: 1110-1115 5 Nauth AM, Orejarena Pacheco JC, Pusch S, Opatz T. Eur J Org Chem 2017; 2017: 6966-6974 6 Mishra AK, Parvari G, Cohen I, Fridman N, Eichen Y, Szpilman AMJ. Coordinat Chem 2018; 71: 2082-2089 7a Yang Z, Liu Y, Cao K, Zhang X, Jiang H, Li J. Beilstein J Org Chem 2021; 17: 771-799 7b Politzer P, Murray JS, Clark T. Phys Chem Chem Phys 2013; 15: 11178-11189 7c Clark T, Hennemann M, Murray JS, Politzer PJ. Mol Mod 2007; 13: 291-296 7d Crisenza GEM, Mazzarella D, Melchiorre P. J Am Chem Soc 2020; 142: 5461-5476 8a Cohen I, Mishra AK, Parvari G. et al. Chem Commun 2017; 53: 10128-10131 8b Mishra AK, Parvari G, Santra SK. et al. Angew Chem Int Ed 2021; 60: 12406-12412 9 Bourboula A, Mountanea OG, Krasakis G. et al. Eur J Org Chem 2023; 26: e202300008 10 Mountanea OG, Psathopoulou D, Mantzourani C. et al. Chem Eur J 2023; 29: e202300556 11a Schultz DM, Yoon TP. Science 2014; 343: 1239176 11b Oelgemöller M. Chem Rev 2016; 116: 9664-9682 12 Santra SK, Szpilman AM. J Org Chem 2021; 86: 1164-1171 13 James MJ, Strieth-Kalthoff F, Sandfort F, Klauck FJR, Wagener F, Glorius F. Chem Eur J 2019; 25: 8240-8244 14 Batra A, Singh KN. Eur J Org Chem 2020; 2020: 6676-6703 15 Perreault S, Spino C. Org Lett 2006; 8: 4385-4388 16 Routsi EA, Mantzourani C, Rrapi M. et al. ChemPlusChem 2024; 89: e202400019 Supplementary Material Supplementary Material Supplementary Material (PDF) (opens in new window)
