Nucleophilic Trifluoromethylation Reactions Involving Copper(I) Species: From Organometallic Insights to Scope

Ángel L. Mudarra; Sara Martínez de Salinas; Mónica H. Pérez-Temprano

doi:10.1055/s-0037-1611776

Synthesis, Table of Contents

Synthesis 2019; 51(14): 2809-2820
DOI: 10.1055/s-0037-1611776

short review

Nucleophilic Trifluoromethylation Reactions Involving Copper(I) Species: From Organometallic Insights to Scope

Ángel L. Mudarra

^aInstitute of Chemical Research of Catalonia (ICIQ) Avgda. Països Catalans, 16, 43007 Tarragona, Spain Email: mperez@iciq.es

^bDepartment de Química Analítica I Química Orgànica, Universitat Rovira i Virgili, C/Marcel·li Domingo s/n, 43007 Tarragona, Spain

,

Sara Martínez de Salinas

^aInstitute of Chemical Research of Catalonia (ICIQ) Avgda. Països Catalans, 16, 43007 Tarragona, Spain Email: mperez@iciq.es

,

Mónica H. Pérez-Temprano *

^aInstitute of Chemical Research of Catalonia (ICIQ) Avgda. Països Catalans, 16, 43007 Tarragona, Spain Email: mperez@iciq.es

› Author Affiliations

Abstract

All articles of this category

^§These authors contributed equally to this work.

Published as part of the Bürgenstock Special Section 2018 Future Stars in Organic Chemistry

Abstract

Over the last decades, trifluoromethyl copper(I) complexes have played a key role as reactive species in C–CF₃ bond-forming reactions. This Short Review not only covers selected examples of relevant copper-mediated or catalyzed nucleophilic trifluoromethylation reactions, which is one of the most active fields in organic synthesis, but also provides a comprehensive picture of the real behavior of these copper species, including ubiquitous cuprates, in the reaction media.

1 Introduction

2 Historical Perspective of the Identification of Relevant Trifluoro-

methyl Copper(I) Species

3 In Situ Generation of Active Trifluoromethyl Copper(I) Species

4 Well-Defined Active Trifluoromethyl Copper(I) Complexes

5 Recent Advances on the Performance of Trifluoromethylation

Protocols

6 Conclusions

Key words

trifluoromethylation - copper - ate-type complexes - catalysis - organometallic chemistry

Full Text

References

References

1a Schlosser M. Angew. Chem. Int. Ed. 2006; 45: 5432
1b Mueller 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 Ni C, Hu J. Chem. Soc. Rev. 2016; 45: 5441
1e Orsi DL, Altman RA. Chem. Commun. 2017; 7168

For selected recent reviews on trifluoromethylation, see:

2a Furuya T, Kamlet AS, Ritter T. Nature 2011; 473: 470
2b Tomashenko OA, Grushin VV. Chem. Rev. 2011; 111: 4475
2c Studer A. Angew. Chem. Int. Ed. 2012; 51: 8950
2d García-Monforte MA, Martínez-Salvador S, Menjón B. Eur. J. Inorg. Chem. 2012; 4945
2e Ye Y, Sanford MS. Synlett 2012; 23: 2005
2f Wu X.-F, Neumann H, Beller M. Chem. Asian J. 2012; 7: 1744
2g Wang H, Vicic DA. Synlett 2013; 24: 1887
2h Barata-Vallejo S, Lantaño B, Postigo A. Chem. Eur. J. 2014; 20: 16806
2i Charpentier J, Früh N, Togni A. Chem. Rev. 2015; 115: 650
2j Liu X, Xu C, Wang M, Liu Q. Chem. Rev. 2015; 115: 683
2k Yang X, Wu T, Phipps RJ, Toste FD. Chem. Rev. 2015; 115: 826
2l Alonso C, Martínez de Marigorta E, Rubiales G, Palacios F. Chem. Rev. 2015; 115: 1847

3a McLoughlin VC. R, Thrower J. U. S. Patent 3408411, 1968
3b McLoughlin VC. R, Thrower J. Tetrahedron 1969; 25: 5921

For representative examples on the synthesis and reactivity of CuCF₃ complexes, see:

4a Wiemers DM, Burton DJ. J. Am. Chem. Soc. 1986; 108: 832
4b Dubinina GG, Furutachi H, Vicic DA. J. Am. Chem. Soc. 2008; 130: 8600
4c Dubinina GG, Ogikubo J, Vicic DA. Organometallics 2008; 27: 6233
4d Morimoto H, Tsubogo T, Litvinas ND, Hartwig JF. Angew. Chem. Int. Ed. 2011; 50: 3793
4e Tomashenko OA, Escudero-Adán EC, Martínez-Belmonte M, Grushin VV. Angew. Chem. Int. Ed. 2011; 50: 7655
4f Zanardi A, Novikov MA, Martin E, Benet-Buchholz J, Grushin VV. J. Am. Chem. Soc. 2011; 133: 20901
4g Litvinas ND, Fier PS, Hartwig JF. Angew. Chem. Int. Ed. 2012; 51: 536
4h Novák P, Lishchynskyi A, Grushin VV. J. Am. Chem. Soc. 2012; 134: 16167
4i Konovalov AI, Lishchynskyi A, Grushin VV. J. Am. Chem. Soc. 2014; 136: 13410
4j Lishchynskyi A, Berthon G, Grushin VV. Chem. Commun. 2014; 10237
4k Mormino MG, Fier PS, Hartwig JF. Org. Lett. 2014; 16: 1744
4l Nebra N, Grushin VV. J. Am. Chem. Soc. 2014; 136: 16998
4m Morstein J, Hou H, Cheng C, Hartwig JF. Angew. Chem. Int. Ed. 2016; 55: 8054

5 Martínez de Salinas S, Mudarra AL, Odena C, Martínez Belmonte M, Benet-Buchholz J, Maseras F, Pérez-Temprano MH. Chem. Eur. J.
6 Wiemers DM, Burton DJ. J. Am. Chem. Soc. 1986; 108: 832; and references cited therein

7a Willert-Porada MA, Burton DJ, Baenziger NC. J. Chem. Soc., Chem. Commun. 1989; 1633
7b Burton DJ, Wiemers DM. J. Fluorine Chem. 1985; 29: 359

8 Agnes K, Movchun V, Rodima T, Dansauer T, Rusanov EB, Leito I, Kaljurand I, Koppel J, Pihl V, Koppel I, Ovsjannikov G, Toom L, Mishima M, Medebielle M, Lork E, Röschenthaler G.-V, Koppel IA, Kolomeitsev AA. J. Org. Chem. 2008; 73: 2607

9a Matsui K, Tobita E, Ando M, Kondo K. Chem. Lett. 1981; 1719
9b Carr GE, Chambers RD, Holmes TF, Parker DG. J. Chem. Soc., Perkin Trans. 1 1988; 921

10 Chen Q, Wu S. J. Chem. Soc., Chem. Commun. 1989; 705
11 Knauber T, Arikan F, Röschenthaler G.-V, Gooßen LJ. Chem. Eur. J. 2011; 17: 2689

12a Shono T, Ishifune M, Okada T, Kashimura S. J. Org. Chem. 1991; 56: 2
12b Russell J, Roques N. Tetrahedron 1998; 54: 13771

13 Folléas B, Marek I, Normanta J-F, Saint-Jalmes L. Tetrahedron 2000; 56: 275
14 Lishchynskyi A, Novikov MA, Martin E, Escudero-Adán EC, Novák P, Grushin VV. J. Org. Chem. 2013; 78: 11126
15 Mudarra AL, Martínez de Salinas S, Pérez-Temprano MH. Org. Biomol. Chem. 2019; 17: 1655

16a Barbosa HJ, Collins EA, Hamdouchi C, Hembre EJ, Hipskind PA, Johnston RD, Lu J, Rupp MJ, Takakuwa T, Thompson RC. U. S. Patent 7612067, 2009
16b Lin RW, Davidson RI. Eur. Pat. Appl. EU 307519, 1989
16c Lin RW, Davidson RI. U. S. Patent 4808748, 1989
16d Davidson RI. U. S. Patent 4814480, 1989
16e Langlois BR, Roques N. J. Fluorine Chem. 2007; 128: 1318

17a Li Y, Chen T, Wang H, Zhang R, Jin K, Wang X, Duan C. Synlett 2011; 1713
17b Schareina T, Wu X.-F, Zapf A, Cotté A, Gotta M, Beller M. Top. Catal. 2012; 55: 426
17c Chen M, Buchwald SL. Angew. Chem. Int. Ed. 2013; 52: 11628
17d Lin X, Hou C, Li H, Weng Z. Chem. Eur. J. 2016; 22: 2075

18 Zhao G, Wu H, Xiao Z, Chen Q.-Y, Liu C. RSC Adv. 2016; 6: 50250

19a MacNeil JG. Jr, Burton DJ. J. Fluorine Chem. 1991; 55: 225
19b Duan J.-X, Su D.-B, Wu J.-P, Chen Q.-Y. J. Fluorine Chem. 1994; 66: 167

20 Prakash GK. S, Hu J, Olah GA. Org. Lett. 2003; 5: 3253
21 Serizawa H, Aikawa K, Mikami K. Chem. Eur. J. 2013; 19: 17692
22 Li X, Zhao J, Zhang L, Hu M, Wang L, Hu J. Org. Lett. 2015; 17: 298

23a Burton DJ, Yang ZY. Tetrahedron 1992; 48: 189
23b Morrison JA. Adv. Organomet. Chem. 1993; 35: 211

24 Kondratenko NV, Vechirko EP, Yagupolskii LM. Synthesis 1980; 932
25 Burton DJ, Wiemers DM. J. Am. Chem. Soc. 1985; 107: 5014

26a Krause LJ, Morrison JA. J. Am. Chem. Soc. 1981; 103: 2995
26b Krause LJ, Morrison JA. J. Chem. Soc., Chem. Commun. 1981; 1282
26c Nair HK, Morrison JA. Inorg. Chem. 1989; 28: 2816
26d Galiotos JK, Morrison JA. Organometallics 2000; 19: 2603

27 Popov I, Lindeman S, Daugulis O. J. Am. Chem. Soc. 2011; 133: 9286
28 Nakamura Y, Fujiu M, Murase T, Itoh Y, Serizawa H, Aikawa K, Mikami K. Beilstein J. Org. Chem. 2013; 9: 2404
29 Aikawa K, Nakamura Y, Yokota Y, Toya W, Mikami K. Chem. Eur. J. 2015; 21: 96
30 Urata H, Fuchikami T. Tetrahedron 1991; 32: 91
31 Oishi M, Kondo H, Amii H. Chem. Commun. 2009; 1909

32a Mitsudera H, Li C.-J. Tetrahedron Lett. 2011; 52: 1898
32b Xu J, Xiao B, Xie C.-Q, Luo D.-F, Liu L, Fu Y. Angew. Chem. Int. Ed. 2012; 124: 12719
32c Gonda Z, Kovács S, Wéber C, Gáti T, Mészáros A, Kotschy A, Novák Z. Org. Lett. 2014; 16: 4268

33 Hu M, Ni C, Hu J. J. Am. Chem. Soc. 2012; 134: 15257
34 Chu L, Qing F.-L. Acc. Chem. Res. 2014; 47: 1513

35a Chu L, Qing F.-L. J. Am. Chem. Soc. 2010; 132: 7262
35b Chu L, Qing F.-L. Org. Lett. 2010; 12: 5060

36 Jiang X, Chu L, Qing F.-L. J. Org. Chem. 2012; 77: 1251
37 Jover J, Maseras F. Chem. Commun. 2013; 10486
38 Weske S, Schoop R, Koszinowski K. Chem. Eur. J. 2016; 22: 11310
39 Sanhueza IA, Nielsen MC, Ottiger M, Schoenebeck F. Helv. Chim. Acta 2012; 95: 2231
40 Khan BA, Buba AE, Gooßen LJ. Chem. Eur. J. 2012; 18: 1577
41 Geri JB, Wolfe MM. W, Szymczak NK. Angew. Chem. Int. Ed. 2018; 57: 1381

42a Chan DM. T, Monaco KL, Wang R.-P, Winters MP. Tetrahedron 1998; 39: 2933
42b Lam PY. S, Clark CG, Saubern S, Adams J, Winters MP, Chan DM. T, Combs A. Tetrahedron 1998; 39: 2941

43 https://www.sigmaaldrich.com/catalog/product/aldrich/ 777692?lang=es&region=ES
44 Usui Y, Noma J, Hirano M, Komiya S. Inorg. Chim. Acta 2000; 309: 151
45 Kaplan PT, Loyd JA, Chin MT, Vicic DA. Beilstein J. Org. Chem. 2017; 13: 2297