Synthesis, Table of Contents Synthesis 2023; 55(12): 1886-1892DOI: 10.1055/a-2004-6031 paper Special Issue dedicated to Prof. Alain Krief Copper-Catalyzed Radical Cascade Annulation for the Preparation of Difluorinated Pyrrolidines and Piperidines Michela Maria Marchese , Sebastian Strähler , Lucian Ghiba , Olivier Riant ∗ Recommend Article Abstract Buy Article All articles of this category This article is dedicated to Professor Alain Krief on the occasion of his 80th birthday Abstract In this work, we developed a one-pot, copper-catalyzed aminodifluoroalkylation of enylaniline derivatives. This approach allows the catalytic construction of a broad range of pyrrolidines and piperidines substituted with a gem-difluoro moiety. Key words Key wordspyrrolidine - piperidine - heterocycles - copper - fluorine - catalysis Full Text References References 1 Zhu R, Buchwald SL. J. Am. Chem. Soc. 2012; 134: 12462 For reviews on the importance of fluorine in medicinal chemistry, see: 2a Böhm HJ, Banner D, Bendels S, Kansy M, Kuhn B, Müller K, Obst-Sander U, Stahl M. ChemBioChem 2004; 5: 637 2b Ni C, Hu M, Hu J. Chem. Rev. 2015; 115: 765 2c Müller K, Faeh C, Diederich F. Science 2007; 317: 1881 For some representative examples, see: 3a Qing FL, Liu XY, Ma JA, Shen Q, Song Q, Tang P. CCS Chem. 2022; 4: 2518 3b Ma C, Meng H, He X, Jiang Y, Yu B. Front. Chem. 2022; 10: 1 3c Fu X, Zhang T, Wu J, Sun Y, Wu F. Eur. J. Org. Chem. 2022; e202101542 3d Ma C, Meng H, He X, Jiang Y, Yu B. Front. Chem. 2022; 10: 953978 3e Umemoto T, Yang Y, Hammond GB. Beilstein J. Org. Chem. 2021; 17: 1752 3f Kirk KL. Org. Process Res. Dev. 2008; 12: 305 3g Li M, Wang CT, Qiu YF, Zhu XY, Han YP, Xia Y, Li XS, Liang YM. Chem. Commun. 2018; 54: 5334 For some representative examples, see: 4a Liao J, Ouyang L, Lai Y, Luo R. J. Org. Chem. 2020; 85: 5590 4b Zhu E, Liu XX, Wang AJ, Mao T, Zhao L, Zhang X, He CY. Chem. Commun. 2019; 55: 12259 5 Clark AJ. Eur. J. Org. Chem. 2016; 2231 6 Matyjaszewski K. Macromolecules 2012; 45: 4015 7 Egami H, Kawamura S, Miyazaki A, Sodeoka M. Angew. Chem. Int. Ed. 2013; 52: 7841 8 Zhu R, Buchwald SL. Angew. Chem. Int. Ed. 2013; 52: 12655 9 Lin JS, Xiong YP, Ma CL, Zhao LJ, Tan B, Liu XY. Chem. Eur. J. 2014; 20: 1332 10 He YT, Li LH, Yang YF, Wang YQ, Luo JY, Liu XY, Liang YM. Chem. Commun. 2013; 49: 5687 11 Lin JS, Dong XY, Li TT, Jiang NC, Tan B, Liu XY. J. Am. Chem. Soc. 2016; 138: 9357 12 Kim E, Choi S, Kim H, Cho EJ. Chem. Eur. J. 2013; 19: 6209 13 Wang X, Li M, Yang Y, Guo M, Tang X, Wang G. Adv. Synth. Catal. 2018; 360: 2151 14 Lin JS, Wang FL, Dong XY, He WW, Yuan Y, Chen S, Liu XY. Nat. Commun. 2017; 8: 14841 For our previous work on copper catalysis, see: 15a Chuzel O, Deschamp J, Chausteur C, Riant O. Org. Lett. 2006; 8: 5943 15b Deschamp J, Chuzel O, Hannedouche J, Riant O. Angew. Chem. Int. Ed. 2006; 45: 1292 15c Deschamp J, Riant O. Org. Lett. 2009; 11: 1217 16 Eckenhoff WT, Pintauer T. Dalton Trans. 2011; 4909 17 Fang C, Fantin M, Pan X, De Fiebre K, Coote ML, Matyjaszewski K, Liu P. J. Am. Chem. Soc. 2019; 141: 7486 18a Eckenhoff WT, Pintauer T. Catal. Rev.: Sci. Eng. 2010; 52: 1 18b Guo Q, Wang M, Peng Q, Huo Y, Liu Q, Wang R, Xu Z. ACS Catal. 2019; 9: 4470 18c Li D, Mao T, Huang J, Zhu Q. J. Org. Chem. 2018; 83: 10445 18d Yang Y, Yuan F, Ren X, Wang G, Zhao W, Tang X, Guo M. J. Org. Chem. 2019; 84: 4507 18e Da Y, Han S, Du X, Liu S, Liu L, Li J. Org. Lett. 2018; 20: 5149 18f Wang F, Wang D, Mu X, Chen P, Liu G. J. Am. Chem. Soc. 2014; 136: 10202 19 Singh GS. Adv. Heterocycl. Chem. 2020; 130: 1 Supplementary Material Supplementary Material Supporting Information