(Difluoromethyl)trimethylsilane (TMSCHF2): A Useful Difluoromethylating Nucleophilic Source
Margherita Miele A and Vittorio Pace![https://orcid.org/0000-0003-3037-5930](/media/client/orcid_16x16.png)
A Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria.
B Department of Chemistry, University of Turin, Via P. Giuria 7, 10125 Turin, Italy.
C Corresponding author. Email: vittorio.pace@univie.ac.at
![]() Vittorio Pace has been a full professor of organic chemistry at the University of Torino (Italy) since March 2020. He earned his Ph.D. in chemical sciences at the Complutense University of Madrid (Spain) and, after three post-doctoral stays in Vienna (Austria), Manchester (UK), and Stockholm (Sweden), he started his independent career in Vienna in 2014, launching a group with a strong focus on homologation chemistry. |
Australian Journal of Chemistry 74(8) 623-625 https://doi.org/10.1071/CH21045
Submitted: 16 February 2021 Accepted: 20 April 2021 Published: 19 May 2021
Keywords : fluorination, fluorine, silicon, organosilicon compounds, difluoromethyl, nucleophilic addition, nucleophilic substitution, cross-coupling.
References
[1] M.-C. Belhomme, T. Besset, T. Poisson, X. Pannecoucke, Chem.–Eur. J. 2015, 21, 12836.| Crossref | GoogleScholarGoogle Scholar | 26178870PubMed |
[2] (a) D. E. Yerien, S. Barata-Vallejo, A. Postigo, Chem.–Eur. J. 2017, 23, 14676.
| Crossref | GoogleScholarGoogle Scholar | 28632338PubMed |
(b) T. Hagiwara, T. Fuchikami, Synlett 1995, 717.
| Crossref | GoogleScholarGoogle Scholar |
[3] X. Liu, C. Xu, M. Wang, Q. Liu, Chem. Rev. 2015, 115, 683.
| Crossref | GoogleScholarGoogle Scholar | 24754488PubMed |
[4] Y. Zhao, W. Huang, J. Zheng, J. Hu, Org. Lett. 2011, 13, 5342.
| Crossref | GoogleScholarGoogle Scholar | 21910464PubMed |
[5] D. Chen, C. Ni, Y. Zhao, X. Cai, X. Li, P. Xiao, J. Hu, Angew. Chem. Int. Ed. 2016, 55, 12632.
| Crossref | GoogleScholarGoogle Scholar |
[6] M. Miele, A. Citarella, T. Langer, E. Urban, M. Zehl, W. Holzer, L. Ielo, V. Pace, Org. Lett. 2020, 22, 7629.
| Crossref | GoogleScholarGoogle Scholar | 32910659PubMed |
[7] (a) M. Miele, A. Citarella, N. Micale, W. Holzer, V. Pace, Org. Lett. 2019, 21, 8261.
| Crossref | GoogleScholarGoogle Scholar | 31599599PubMed |
(b) For the synthesis of mixed dihaloketones, see: S. Touqeer, R. Senatore, M. Malik, E. Urban, V. Pace, Adv. Synth. Catal. 2020, 362, 5056.
| Crossref | GoogleScholarGoogle Scholar |
[8] (a) V. Pace, S. Monticelli, K. de la Vega-Hernandez, L. Castoldi, Org. Biomol. Chem. 2016, 14, 7848.
| Crossref | GoogleScholarGoogle Scholar | 27461156PubMed |
(b) The synthesis of non-fluorinated dihaloacetamides has been accomplished with dihalomethyllithiums; see: V. Pace, L. Castoldi, A. D. Mamuye, W. Holzer, Synthesis 2014, 46, 2897.
| Crossref | GoogleScholarGoogle Scholar |
[9] M. Miele, R. D’Orsi, V. Sridharan, W. Holzer, V. Pace, Chem. Commun. 2019, 55, 12960.
| Crossref | GoogleScholarGoogle Scholar |
[10] P. S. Fier, J. F. Hartwig, J. Am. Chem. Soc. 2012, 134, 5524.
| Crossref | GoogleScholarGoogle Scholar | 22397683PubMed |
[11] J. Wu, Y. Gu, X. Leng, Q. Shen, Angew. Chem. Int. Ed. 2015, 54, 7648.
| Crossref | GoogleScholarGoogle Scholar |
[12] Y. Gu, X. Leng, Q. Shen, Nat. Commun. 2014, 5, 5405.
| Crossref | GoogleScholarGoogle Scholar | 25377759PubMed |
[13] D. M. Ferguson, C. A. Malapit, J. R. Bour, M. S. Sanford, J. Org. Chem. 2019, 84, 3735.
| Crossref | GoogleScholarGoogle Scholar | 30789266PubMed |
[14] D. Zhu, Y. Gu, L. Lu, Q. Shen, J. Am. Chem. Soc. 2015, 137, 10547.
| Crossref | GoogleScholarGoogle Scholar | 26178409PubMed |
[15] (a) B. Bayarmagnai, C. Matheis, K. Jouvin, L. J. Goossen, Angew. Chem. Int. Ed. 2015, 54, 5753.
| Crossref | GoogleScholarGoogle Scholar |
(b) K. Jouvin, C. Matheis, L. J. Goossen, Chem.–Eur. J. 2015, 21, 14324.
| Crossref | GoogleScholarGoogle Scholar |
(c) C. Matheis, K. Jouvin, L. J. Goossen, Org. Lett. 2014, 16, 5984.
| Crossref | GoogleScholarGoogle Scholar |
[16] S.-Q. Zhu, Y.-L. Liu, H. Li, X.-H. Xu, F.-L. Qing, J. Am. Chem. Soc. 2018, 140, 11613.
| Crossref | GoogleScholarGoogle Scholar | 30179476PubMed |