Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2017; 28(01): 19-23
DOI: 10.1055/s-0036-1588643
DOI: 10.1055/s-0036-1588643
synpacts
Toward Sustainable Trifluoromethylation Reactions: Sodium Triflinate under the Spotlight
Further Information
Publication History
Received: 23 September 2016
Accepted after revision: 12 October 2016
Publication Date:
07 November 2016 (online)
![](https://www.thieme-connect.de/media/synlett/201701/lookinside/thumbnails/st-2016-p0633-sp_10-1055_s-0036-1588643-1.jpg)
Dedicated to Dr. Bernard Langlois
Abstract
Direct trifluoromethylation of organic molecules is of upmost importance in medicinal chemistry and agrochemical research. However, finding sustainable reaction conditions should be a priority for chemists to improve the applicability of their research. Herein, we highlight recent advances in transition-metal-free and photochemical activation of sodium triflinate, a commercially available and easy-to-handle source of CF3 radical.
1. Introduction
2. Transition-Metal-Free Activation of Sodium Triflinate
3. Photochemical Activation of Sodium Triflinate
4. Conclusions and Outlook
-
References
- 1a Jeschke P. ChemBioChem 2004; 5: 570
- 1b Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
- 1c Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
- 1d Hunter L. Beilstein J. Org. Chem. 2010; 6: No. 38
- 2a Charpentier J, Früh N, Togni A. Chem. Rev. 2015; 115: 650
- 2b Zhang C. Org. Biomol. Chem. 2014; 12: 6580
- 3 Liu X, Xu C, Wang M, Liu Q. Chem. Rev. 2015; 115: 683
- 4 Zhang C. Adv. Synth. Catal. 2014; 356: 2895
- 5a Tordeux M, Langlois BR, Wakselman C. J. Org. Chem. 1989; 54: 2452
- 5b Langlois BR, Laurent E, Roidot N. Tetrahedron Lett. 1991; 32: 7525
- 6a Ji Y, Brueckl T, Baxter RD, Fujiwara Y, Seiple IB, Su S, Blackmond DG, Baran PS. Proc. Natl. Acad. Sci. U.S.A. 2011; 108: 14411
- 6b Fujiwara Y, Dixon JA, O'Hara F, Daa Funder E, Dixon DD, Rodriguez RA, Baxter RD, Herlé B, Sach N, Collins MR, Ishihara Y, Baran PS. Nature (London, U.K.) 2012; 492: 95
- 6c O'Hara F, Blackmond DG, Baran PS. J. Am. Chem. Soc. 2013; 135: 12122
- 7a Luo H.-Q, Zhang Z.-P, Dong W, Luo X.-Z. Synlett 2014; 25: 1307
- 7b Wu M, Ji X, Dai W, Cao S. J. Org. Chem. 2014; 79: 8984
- 8a Yang Y.-D, Iwamoto K, Tokunaga E, Shibata N. Chem. Commun. 2013; 49: 5510
- 8b Shi L, Yang X, Wang Y, Yang H, Fu H. Adv. Synth. Catal. 2014; 356: 1021
- 8c Wei W, Wen J, Yang D, Liu X, Guo M, Dong R, Wang H. J. Org. Chem. 2014; 79: 4225
- 8d Hang Z, Li Z, Liu Z.-Q. Org. Lett. 2014; 16: 3648
- 8e Zhang L, Li Z, Liu Z.-Q. Org. Lett. 2014; 16: 3688
- 8f Yu J, Yang H, Fu H. Adv. Synth. Catal. 2014; 356: 3669
- 8g Yu Y.-Y, Ranade AR, Georg GI. Adv. Synth. Catal. 2014; 356: 3510
- 8h Shang X.-J, Li Z, Liu Z.-Q. Tetrahedron Lett. 2015; 56: 233
- 8i Ma J.-J, Yi W.-B, Lu G.-P, Cai C. Catal. Sci. Technol. 2016; 6: 417
- 8j Sakamoto R, Kahiwagi H, Selvakumar S, Moteki SA, Maruoka K. Org. Biomol. Chem. 2016; 14: 6417
- 9 Liu C, Lu Q, Huang Z, Zhang J, Liao F, Peng P, Lei A. Org. Lett. 2015; 17: 6034
- 10a Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
- 10b Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
- 11a Nagib DA, MacMillan DW. C. Nature (London, U.K.) 2011; 480: 224
- 11b Mizuta S, Verhoog S, Engle KM, Khotavivattana T, O'Duill M, Wheelhouse K, Rassias G, Médebielle M, Gouverneur V. J. Am. Chem. Soc. 2013; 135: 2505
- 12 Tommasino J.-B, Brondex A, Médebielle M, Thomalla M, Langlois BR, Billard T. Synlett 2002; 1697
- 13 Wilger DJ, Gesmundo NJ, Nicewicz DA. Chem. Sci. 2013; 4: 3160
- 14 Cui L, Matusaki Y, Tada N, Miura T, Uno B, Itoh A. Adv. Synth. Catal. 2013; 355: 2203
- 15 Lefebvre Q, Hoffmann N, Rueping M. Chem. Commun. 2016; 52: 2493
- 16 Zhu L, Wang L.-S, Li B, Fu B, Zhang C.-P, Li W. Chem. Commun. 2016; 52: 6371
- 17 Li L, Mu X, Liu W, Wang Y, Mi Z, Li C.-J. J. Am. Chem. Soc. 2016; 138: 5809
- 18 Li B, Yang C, Xia W. Org. Biomol. Chem. 2016; 14: 5293
- 19 Yu X.-L, Chen J.-R, Chen D.-Z, Xiao W.-J. Chem. Commun. 2016; 52: 8275
- 20 O'Brien AG, Maruyama A, Inokuma Y, Fujita M, Baran PS, Blackmond DG. Angew. Chem. Int. Ed. 2014; 53: 11868
- 21 Fennewald JC, Lipshutz BH. Green Chem. 2014; 16: 1097
- 22 Cambié D, Bottecchia C, Straathof NJ. W, Hessel V, Noël T. Chem. Rev. 2016; 116: 10276
For a pioneering example, see:
For a hydrotrifluoromethylation reaction with Umemoto reagent, see: