Subscribe to RSS
DOI: 10.1055/a-2042-3720
Synthesis of 1-(Trifluoromethyl)alkenes through Transition-Metal-Catalyzed Alkylation and Arylation of 1-Chloro-3,3,3-trifluoroprop-1-ene (HCFO-1233zd)
This work was financially supported by the National Natural Science Foundation of China (21991122), the National Key Research and Development Program of China (2021YFF0701700), and the Science and Technology Commission of Shanghai Municipality (21ZR147660).
Abstract
The synthesis of 1-(trifluoromethyl)alkenes through nickel-catalyzed alkylation/arylation of 1-chloro-3,3,3-trifluoroprop-1-ene (HCFO-1233zd) with alkyl/aryl zinc reagents and cobalt-catalyzed reductive cross-coupling between HCFO-1233zd and aryl bromides has been developed. These approaches feature broad substrate scope, high functional group tolerance, and the use of industrial feedstocks and low-cost nickel/cobalt catalysts, providing facile routes to access 1-(trifluoromethyl)alkenes. Diverse transformations of the resulting 1-(trifluoromethyl)alkenes demonstrated the synthetic utility of the current approaches.
Key words
HCFO-1233zd - nickel catalysis - cobalt catalysis - cross-coupling - 1-(trifluoromethyl)alkeneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2042-3720.
- Supporting Information
Publication History
Received: 13 December 2022
Accepted after revision: 24 February 2023
Accepted Manuscript online:
24 February 2023
Article published online:
23 March 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Tomashenko OA, Grushin VV. Chem. Rev. 2011; 111: 4475
- 2 Alonso C, Martínez de Marigorta E. Rubiales G., Palacios F. 2015; 115: 1847
- 3 Hui R, Zhang S, Tan Z, Wu X, Feng B. Chin. J. Org. Chem. 2017; 37: 3060
- 4 Chen D, Yang W, Yao Y, Yang X, Deng Y, Yang D. Chin. J. Org. Chem. 2018; 38: 2571
- 5 Sicard AJ, Baker RT. Chem. Rev. 2020; 120: 9164
- 6 Miyagawa A, Naka M, Yamazaki T, Kawasaki-Takasuka T. Eur. J. Org. Chem. 2009; 4395
- 7 Naka M, Kawasaki-Takasuka T, Yamazaki T. Beilstein J. Org. Chem. 2013; 9: 2182
- 8 Yamakawa S, Yamamoto T. JP2016/179968 A, 2016
- 9 Mushta O. І, Kremlev MM, Filatov AA, Yagupolskii YL. J. Fluorine Chem. 2020; 232: 109456
- 10 Li Y, Hao M, Chang Y.-C, Liu Y, Wang W.-F, Sun N, Zhu W.-Q, Gao Z. Chin. J. Chem. 2021; 39: 2962
- 11 Petko KI, Filatov A. А, Yagupolskii YL. Chem. Heterocycl. Compd. (Engl. Transl.) 2022; 58: 129
- 12 Grushin VV, Alper H. Chem. Rev. 2002; 94: 1047
- 13 Littke AF, Fu GC. Angew. Chem. Int. Ed. 2002; 41: 4176
- 14 Xu C, Guo W.-H, He X, Guo Y.-L, Zhang X.-Y, Zhang X. Nat. Commun. 2018; 9: 1170
- 15 Kim S, Goldfogel MJ, Gilbert MM, Weix DJ. J. Am. Chem. Soc. 2020; 142: 9902
- 16 Moncomble A, Floch PL, Lledos A, Gosmini C. J. Org. Chem. 2012; 77: 5056
- 17 Davoren JE, Gray DL, Harris AR, Nason DM, Xu W. Synlett 2010; 2490
- 18 Roshandel S, Gurung L, Mathew T, Prakash GK. S. Tetrahedron Lett. 2017; 58: 2842
- 19 Krasovskiy A, Malakhov V, Gavryushin A, Knochel P. Angew. Chem. Int. Ed. 2006; 45: 6040