Direct Trifluoromethylthiolation Reactions Involving Radical Processes

An overview of the most significant radical-based synthetic methods currently available for the preparation of trifluoromethylthiolated compounds is presented.

1 Introduction

2 Early Work: Photochemical Reactions Under UV Irradiation

2.1 Reactions Involving CF₃SH

2.2 Reactions Involving CF₃SCl

2.3 Reactions Involving CF₃SSCF₃

3 Reactions Involving a Nucleophilic SCF₃ Reagent

3.1 Reactions with CuSCF₃

3.2 Reactions with AgSCF₃

4 Reactions Involving an Electrophilic SCF₃ Reagent

4.1 Reactions Involving the Formation of an R^• Radical

4.2 Reactions involving the formation of ^•SCF₃ Radical

5 Conclusion

Key words

trifluoromethythiolation - radicals - silver-mediated oxidative transformations - photoredox catalysis - electrophilic SCF₃ reagents

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Referenzen

References

1a Kirsch P. In Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications. Wiley; New-York: 2013. 2nd ed.
1b Müller K, Faeh C, Diederich F. Science 2007; 317: 1881
1c Bioorganic and Medicinal Chemistry of Fluorine . Begue J.-P, Bonnet-Delpon D. Wiley; Hoboken: 2008
1d Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
1e Berger R, Resnati G, Metrangolo P, Weber E, Hulliger J. Chem. Soc. Rev. 2011; 40: 3496
1f Wang J, Sanchez-Rosello M, Acena JL, delPozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H. Chem. Rev. 2014; 114: 2432

2 Leo A, Hansch C, Elkins D. Chem. Rev. 1971; 71: 525

For selected reviews, see:

3a Leroux F, Jeschke P, Schlosser M. Chem. Rev. 2005; 105: 827
3b Boiko VN. Beilstein J. Org. Chem. 2010; 6: 880
3c Tlili A, Billard T. Angew. Chem. Int. Ed. 2013; 52: 6818
3d Toulgoat F, Alazet S, Billard T. Eur. J. Org. Chem. 2014; 2415
3e Xu X.-H, Matsuzaki K, Shibata N. Chem. Rev. 2015; 115: 731
3f Barata-Vallejo S, Bonesi S, Postigo A. Org. Biomol. Chem. 2016; 14: 7150
3g Zheng H, Huang Y, Weng Z. Tetrahedron Lett. 2016; 57: 1397
3h Chachignon H, Cahard D. Chin. J. Chem. 2016; 34: 445

4 Bolman PS. H, Safarik I, Stiles DA, Tyerman WJ. R, Strausz OP. Can. J. Chem. 1970; 48: 3872
5 Harris JF. Jr, Stacey FW. J. Am. Chem. Soc. 1961; 83: 840
6 Harris JF. Jr. du Pont de Nemours Patent US 3522293, 1970
7 Harris JF. Jr. J. Am. Chem. Soc. 1962; 84: 3148
8 Harris JF. Jr. J. Org. Chem. 1966; 31: 931
9 Munavalli S, Rohrbaugh DK, Berg FJ, McMahon LR, Longo FR, Durst HD. Phosphorus Sulfur Silicon Relat. Elem. 2002; 177: 1117
10 Haran G, Sharp DW. A. J. Chem. Soc., Perkin Trans. 1 1972; 34
11 Dear RE. A, Gilbert EE. J. Fluorine Chem. 1974; 4: 107
12 Munavalli S. Heteroatom Chem. 1992; 3: 189
13 Munavalli S, Rossman DI, Rohrbaugh DK, Ferguson CP, Durst HD. J. Fluorine Chem. 1996; 76: 7
14 Munavalli S, Wagner GW, Bashir-Hashemi A, Rohrbaugh DK, Durst HD. Synth. Commun. 1997; 27: 2847
15 Munavalli S, Bashir-Hashemi A, Rohrbaugh DK, Durst HD. Phosphorus Sulfur Silicon Relat. Elem. 2006; 181: 435

16a Man EH, Coffman DD, Muetterties EL. J. Am. Chem. Soc. 1959; 81: 3575
16b Emeléus HJ, MacDuffie DE. J. Chem. Soc. 1961; 2597

17a Orda VV, Yagupolskii LM, Bystrov VF, Stepanyati AU. Zh. Obshch. Khim. 1965; 35: 1628
17b Petrova TD, Platnov VE, Shcheyoleva LN, Maksimov AM, Haas A, Schelvis M, Lieb M. J. Fluorine Chem. 1996; 79: 13
17c Adams DJ, Clark JH. J. Org. Chem. 2000; 65: 1456

18 Teverovskiy G, Surry DS, Buchwald SL. Angew. Chem. Int. Ed. 2011; 50: 7312
19 Yin F, Wang X.-S. Org. Lett. 2014; 16: 1128
20 Fuentes N, Kong W, Fernández-Sánchez L, Merino E, Nevado C. J. Am. Chem. Soc. 2015; 137: 964
21 Ji M, Wu Z, Yu J, Wan X, Zhu C. Adv. Synth. Catal. 2017; 359: 1959
22 Qiu Y.-F, Zhu X.-Y, Li Y.-X, He Y.-T, Yang F, Wang J, Hua H.-L, Zheng L, Wang L.-C, Liu X.-Y, Liang YM. Org. Lett. 2015; 17: 3694
23 Jin D.-P, Gao P, Chen D.-Q, Chen S, Wang J, Liu X.-Y, Liang Y.-M. Org. Lett. 2016; 18: 3486
24 Guo C.-H, Chen D.-Q, Chen S, Liu X.-Y. Adv. Synth. Catal. 2017; 359: 2901
25 Li H, Liu S, Huang Y, Xu X.-H, Qing F.-L. Chem. Commun. 2017; 53: 10136
26 Wu W, Dai W, Ji X, Cao S. Org. Lett. 2016; 18: 2918
27 Zhu L, Wang G, Guo Q, Xu Z, Zhang D, Wang R. Org. Lett. 2014; 16: 5390
28 Cheng Z.-F, Tao T.-T, Feng Y.-S, Tang W.-K, Xu J, Dai J.-J, Xu H.-J. J. Org. Chem. 2018; 83: 499
29 Pan S, Huang Y, Xu X.-H, Qing F.-L. Org. Lett. 2017; 19: 4624
30 Pan S, Li H, Huang Y, Xu X.-H, Qing F.-L. Org. Lett. 2017; 19: 3247
31 Zhang K, Liu J.-B, Qing F.-L. Chem. Commun. 2014; 50: 14157
32 Guo S, Zhang X, Tang P. Angew. Chem. Int. Ed. 2015; 54: 4065
33 Wu H, Xiao Z, Wu J, Guo Y, Xiao J.-C, Liu C, Chen Q.-Y. Angew. Chem. Int. Ed. 2015; 54: 4070
34 Huang F.-Q, Wang Y.-W, Sun J.-G, Xie J, Qi L.-W, Zhang B. RSC Adv. 2016; 6: 52710
35 Hu F, Shao X, Zhu D, Lu L, Shen Q. Angew. Chem. Int. Ed. 2014; 53: 6105
36 Candish L, Pitzer L, Gómez-Suárez A, Glorius F. Chem. Eur. J. 2016; 22: 4753
37 Czaplyski WL, Na CG, Alexanian EJ. J. Am. Chem. Soc. 2016; 138: 13854
38 Koziakov D, Majek M, Jacobi von Wangelin A. Eur. J. Org. Chem. 2017; 6722
39 Yang T, Lu L, Shen Q. Chem. Commun. 2015; 51: 5479
40 Fang J, Wang Z.-K, Wu S.-W, Shen W.-G, Ao G.-Z, Liu F. Chem. Commun. 2017; 53: 7638
41 Mukherjee S, Maji B, Tlahuext-Aca A, Glorius F. J. Am. Chem. Soc. 2016; 138: 16200
42 Honeker R, Garza-Sanchez RA, Hopkinson MN, Glorius F. Chem. Eur. J. 2016; 22: 4395
43 Dagousset G, Simon C, Anselmi E, Tuccio B, Billard T, Magnier E. Chem. Eur. J. 2017; 23: 4282
44 Li Y, Koike T, Akita M. Asian J. Org. Chem. 2017; 6: 445