RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2023; 55(12): 1886-1892
DOI: 10.1055/a-2004-6031
DOI: 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
We are deeply appreciative of financial support from the Fonds de la Recherche Scientifique (FNRS, PDR funding for M. Marchese; PDR T.0194.19), the Fonds pour la formation à la Recherche dans l’Industrie et dans l’Agriculture (FRIA, Sebastian Strähler), and the Université catholique de Louvain.
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2004-6031.
- Supporting Information
Publikationsverlauf
Eingereicht: 16. November 2022
Angenommen nach Revision: 29. Dezember 2022
Accepted Manuscript online:
29. Dezember 2022
Artikel online veröffentlicht:
02. Februar 2023
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Zhu R, Buchwald SL. J. Am. Chem. Soc. 2012; 134: 12462
- 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
- 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
- 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
- 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
For reviews on the importance of fluorine in medicinal chemistry, see:
For some representative examples, see:
For some representative examples, see:
For our previous work on copper catalysis, see: