Introduction of Functionalized Difluoromethylated Building Blocks Mediated or Catalyzed by Copper

Xavier Pannecoucke; Thomas Poisson

doi:10.1055/s-0035-1562784

Synlett, Inhaltsverzeichnis

Synlett 2016; 27(16): 2314-2326
DOI: 10.1055/s-0035-1562784

account

Introduction of Functionalized Difluoromethylated Building Blocks Mediated or Catalyzed by Copper

Autor*innen

Xavier Pannecoucke

Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA, (UMR 6014), 76000 Rouen, France eMail: thomas.poisson@insa-rouen.fr
Thomas Poisson*

Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA, (UMR 6014), 76000 Rouen, France eMail: thomas.poisson@insa-rouen.fr

Abstract

Alle Artikel dieser Rubrik

Abstract

This account summarizes our recent progress on the copper-catalyzed direct introduction of functionalized difluoromethylated building blocks, and more particularly, the CF₂CO₂Et motif. We also discuss how this work led us to develop new copper-mediated methodologies to introduce the CF₂PO(OR)₂ motif, a valuable phosphate bioisostere.

1 Introduction

2 Copper-Catalyzed Introduction of the CF₂CO₂Et Residue

3 New Developments Toward the Introduction of the CF₂PO(OEt)₂ Motif

4 Conclusion and Outlook

Key words

fluorine - copper - difluoromethylene - phosphate mimic - C–H bond functionalization

Volltext

Referenzen

References
1 O’Hagan D. Chem. Soc. Rev. 2008; 37: 308

2a Wang J, Sánchez-Roselló M, Aceña JL, del Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H. Chem. Rev. 2014; 114: 2432
2b Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
2c Ilardi EA, Vitaku E, Njardarson JT. J. Med. Chem. 2014; 57: 2832
2d Ilardi EA, Vitaku E, Njardarson JT. J. Chem. Educ. 2013; 90: 1403

3a Böhm H.-J, Banner D, Bendels S, Kansy M, Kuhn B, Müller K, Obst-Sander U, Stahl M. ChemBioChem 2004; 5: 637
3b Müller K, Faeh C, Diederich F. Science 2007; 317: 1881

For selected reviews, see:

4a Merino E, Nevado C. Chem. Soc. Rev. 2014; 43: 6598
4b Egami H, Sodeoka M. Angew. Chem. Int. Ed. 2014; 53: 8294
4c Liang T, Neumann CN, Ritter T. Angew. Chem. Int. Ed. 2013; 52: 8214
4d Furuya T, Kamlet AS, Ritter T. Nature 2011; 473: 470
4e Besset T, Poisson T, Pannecoucke X. Eur. J. Org. Chem. 2015; 2765
4f Zeng Y, Ni C, Hu J. Chem. Eur. J. 2015; 22: 3210

5a Campbell MG, Ritter T. Chem. Rev. 2015; 115: 612
5b Ritter T, Furuya T, Kuttruff CA. Curr. Opin. Drug Discovery Dev. 2008; 11: 803

For recent reviews, see:

6a Liu X, Xu C, Wang M, Liu Q. Chem. Rev. 2015; 115: 683
6b Charpentier J, Früh N, Togni A. Chem. Rev. 2015; 115: 650
6c Tomashenko OA, Grushin VV. Chem. Rev. 2011; 111: 4475

For recent reviews, see:

7a Xu X.-H, Matsuzaki K, Shibata N. Chem. Rev. 2015; 115: 731
7b Toulgoat F, Alazet S, Billard T. Eur. J. Org. Chem. 2014; 2415

8a Besset T, Poisson T, Pannecoucke X. Chem. Eur. J. 2014; 20: 16830
8b Chen P, Liu G. Synthesis 2013; 45: 2919
8c Wu X.-F, Neumann H, Beller M. Chem. Asian J. 2012; 7: 1744
8d Liu H, Gu Z, Jiang X. Adv. Synth. Catal. 2013; 355: 617

9a Belhomme M.-C, Besset T, Poisson T, Pannecoucke X. Chem. Eur. J. 2015; 21: 12836
9b Ni C, Zhu L, Hu J. Acta Chim. Sinica 2015; 73: 90
9c Xu P, Guo S, Wang L, Tang P. Synlett 2014; 26: 36
9d Gao B, Ni C, Hu J. Chimia 2014; 68: 414
9e Chen B, Vicic DA. Top. Organomet. Chem. 2014; 52: 113

For related papers from our group reporting the use of BrCF₂CO₂Et, see:

10a Poisson T, Belhomme M.-C, Pannecoucke X. J. Org. Chem. 2012; 77: 9277
10b Fontenelle CQ, Conroy M, Light M, Poisson T, Pannecoucke X, Linclau B. J. Org. Chem. 2014; 79: 4186
10c Lemonnier G, Poisson T, Couve-Bonnaire S, Jubault P, Pannecoucke X. Eur. J. Org. Chem. 2013; 3278
10d Besset T, Poisson T, Pannecoucke X. Eur. J. Org. Chem. 2014; 7220

For selected examples, see:

11a Fujikawa K, Fujioka Y, Kobayashi A, Amii H. Org. Lett. 2011; 13: 5560
11b Fujikawa K, Kobayashi A, Amii H. Synthesis 2012; 44: 3015
11c Taguchi T, Kitagawa O, Morikawa T, Nishiwaki T, Uehara H, Endo H, Kobayashi Y. Tetrahedron Lett. 1986; 27: 6103
11d Schwaebe MK, McCarthy JR, Whitten JP. Tetrahedron Lett. 2000; 41: 791
11e Qi Q, Shen Q, Lu L. J. Am. Chem. Soc. 2012; 134: 6548
11f Ashwood MS, Cottrell IF, Cowden CJ, Wallace DJ, Davies AJ, Kennedy DJ, Dolling UH. Tetrahedron Lett. 2002; 43: 9271

12a Murakami S, Ishii H, Tajima T, Fuchigami T. Tetrahedron 2006; 62: 3761
12b Ohtsuka Y, Yamakawa T. Tetrahedron 2011; 67: 2323

13 Leclerc E, Pannecoucke X, Ethève-Quelquejeu M, Sollogoub M. Chem. Soc. Rev. 2013; 42: 4270 ; and references cited therein

For selected references from our group, see:

14a Colombel S, Sanselme M, Leclerc E, Quirion J.-C, Pannecoucke X. Chem. Eur. J. 2011; 17: 5238
14b Colombel S, Van Hijfte N, Poisson T, Leclerc E, Pannecoucke X. Chem. Eur. J. 2013; 19: 12778
14c Colombel S, Van Hijfte N, Poisson T, Pannecoucke X, Monneaux F, Leclerc E. J. Fluorine Chem. 2015; 173: 84
14d Leclerc E, Pannecoucke X. C. R. Chimie 2012; 15: 57

For selected examples, see:

15a Poulain F, Serre A.-L, Lalot J, Leclerc E, Quirion J.-C. J. Org. Chem. 2008; 73: 2435
15b Moreno B, Quehen C, Rose-Hélène M, Leclerc E, Quirion J.-C. Org. Lett. 2007; 9: 2477
15c Poulain F, Leclerc E, Quirion J.-C. Tetrahedron Lett. 2009; 50: 1803
15d Hirai G, Watanabe T, Yamaguchi K, Miyagi T, Sodeoka M. J. Am. Chem. Soc. 2007; 129: 15420
15e Berber H, Brigaud T, Lefebvre O, Plantier-Royon R, Portella C. Chem. Eur. J. 2001; 7: 903

For examples of α-selectivity, see:

16a Gøgsig TM, Kleimark J, Nilsson Lill SO, Korsager S, Lindhardt AT, Norrby P.-O, Skrydstrup T. J. Am. Chem. Soc. 2012; 134: 443
16b Mo J, Xiao J. Angew. Chem. Int. Ed. 2006; 45: 4152
16c Larhed M, Hallberg A. J. Org. Chem. 1997; 62: 7858

For examples and discussion regarding the α/β selectivity, see:

16d Andersson C.-M, Hallberg A. J. Org. Chem. 1987; 52: 3529
16e Nilsson P, Larhed M, Hallberg A. J. Am. Chem. Soc. 2001; 123: 8217
16f Cabri W, Candiani I, Bedeschi A. J. Org. Chem. 1993; 58: 7421
16g Datta GK, von Schenck H, Hallberg A, Larhed M. J. Org. Chem. 2006; 71: 3896

17 Ribas X, Calle C, Poater A, Casitas A, Gómez L, Xifra R, Parella T, Benet-Buchholz J, Schweiger A, Mitrikas G, Solà M, Llobet A, Stack TD. P. J. Am. Chem. Soc. 2010; 132: 12299 ; and references cited therein
18 Phipps RJ, Grimster NP, Gaunt MJ. J. Am. Chem. Soc. 2008; 130: 8172
19 Belhomme M.-C, Poisson T, Pannecoucke X. Org. Lett. 2013; 15: 3428

20a Wegert A, Miethchen R, Hein M, Reinke H. Synthesis 2005; 1850
20b Miethchen R, Hein M, Reinke H. Eur. J. Org. 1998; 919
20c Wegert A, Hein M, Reinke H, Hoffmann N, Miethchen R. Carbohydr. Res. 2006; 341: 2641

21 Belhomme M.-C, Dru D, Xiong H.-Y, Cahard D, Besset T, Poisson T, Pannecoucke X. Synthesis 2014; 46: 1859
22 We cannot preclude that the reductive elimination occurred before the deprotonation step.

For a review, see:

23a Gigant N, Chausset-Boissarie L, Gillaizeau I. Chem. Eur. J. 2014; 20: 7548
23b Gigant N, Chausset-Boissarie L, Belhomme M.-C, Poisson T, Pannecoucke X, Gillaizeau I. Org. Lett. 2013; 15: 278
23c Gigant N, Chausset-Boissarie L, Gillaizeau I. Org. Lett. 2013; 15: 816
23d Gigant N, Gillaizeau I. Org. Lett. 2012; 14: 4622
23e Gigant N, Gillaizeau I. Org. Lett. 2012; 14: 3304
23f Gigant N, Dequirez G, Retailleau P, Gillaizeau I, Dauban P. Chem. Eur. J. 2011; 18: 90

24 Caillot G, Dufour J, Belhomme M.-C, Poisson T, Grimaud L, Pannecoucke X, Gillaizeau I. Chem. Commun. 2014; 50: 5887
25 Belhomme M.-C, Poisson T, Pannecoucke X. J. Org. Chem. 2014; 79: 7205
26 Mishra S, Mondal P, Ghosh M, Mondal S, Hajra A. Org. Biomol. Chem. 2016; 14: 1432
27 Shao C, Shi G, Zhang Y, Pan S, Guan X. Org. Lett. 2015; 17: 2652

For related procedures, see:

28a Kim YS. J. Korean Chem. Soc. 1963; 7: 189
28b Battais A, Boutevin B, Pietrasanta Y. J. Fluorine Chem. 1979; 14: 467

29 Belhomme M.-C, Bayle A, Poisson T, Pannecoucke X. Eur. J. Org. Chem. 2015; 1719
30 Romanenko VD, Kukhar VP. Chem. Rev. 2006; 106: 3868
31 Ivanova MV, Bayle A, Besset T, Pannecoucke X, Poisson T. Chem. Eur. J. 2016; 22: 10284
32 Blackburn GM, Kent DE, Kolkmann F. J. Chem. Soc., Chem. Commun. 1981; 1188

33a Bialy L, Waldmann H. Angew. Chem. Int. Ed. 2005; 44: 3814
33b Combs AP. J. Med. Chem. 2010; 53: 2333
33c Burke TR, Smyth MS, Otaka A, Nomizu M, Roller PP, Wolf G, Case R, Shoelson SE. Biochemistry 1994; 33: 6490
33d Ong JX, Yap CW, Ang WH. Inorg. Chem. 2012; 51: 12483
33e Morlacchi P, Mandal PK, McMurray JS. ACS Med. Chem. Lett. 2014; 5: 69
33f Bahta M, Lountos GT, Dyas B, Kim S.-E, Ulrich RG, Waugh DS, Burke TR. Jr. J. Med. Chem. 2011; 54: 2933

For selected recent examples, see:

34a Gu J.-W, Zhang X. Org. Lett. 2015; 17: 5384
34b Feng Z, Chen F, Zhang X. Org. Lett. 2012; 14: 1938
34c Feng Z, Xiao Y.-L, Zhang X. Org. Chem. Front. 2016; 3: 466
34d Feng Z, Xiao Y.-L, Zhang X. Org. Chem. Front. 2014; 1: 113
34e Feng Z, Min Q.-Q, Xiao Y.-L, Zhang B, Zhang X. Angew. Chem. Int. Ed. 2014; 53: 1669
34f Xie J, Zhang T, Chen F, Mehrkens N, Rominger F, Rudolph M, Hashmi AS. K. Angew. Chem. Int. Ed. 2016; 55: 2934
34g Wang L, Wei X.-J, Lei W.-L, Chen H, Wu L.-Z, Liu Q. Chem. Commun. 2014; 50: 15916

35a Danoun G, Bayarmagnai B, Grünberg MF, Gooßen LJ. Angew. Chem. Int. Ed. 2013; 52: 7972
35b Bayarmagnai B, Matheis C, Risto E, Gooßen LJ. Adv. Synth. Catal. 2014; 356: 2343
35c Danoun G, Bayarmagnai B, Gruenberg MF, Gooßen LJ. Chem. Sci. 2014; 5: 1312
35d Jouvin K, Matheis C, Gooßen LJ. Chem. Eur. J. 2015; 21: 14324
35e Bayarmagnai B, Matheis C, Jouvin K, Gooßen LJ. Angew. Chem. Int. Ed. 2015; 54: 5753

36 For an early report of the formation of the CuCF₂PO(OEt)₂ species, see: Guneratne RD, Burton DJ. J. Fluorine Chem. 1999; 98: 11

For selected examples, see:

37a Jiang X, Chu L, Qing F.-L. New J. Chem. 2013; 37: 1736
37b Jiang X, Chu L, Qing F.-L. Org. Lett. 2012; 14: 2870
37c Alexandrova AV, Beier P. J. Fluorine Chem. 2009; 130: 493

38 Delaunay T, Poisson T, Jubault P, Pannecoucke X. J. Fluorine Chem. 2015; 171: 56

39a Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
39b Yusubov MS, Maskaev AV, Zhdankin VV. ARKIVOC 2011; (i): 370
39c Yoshimura A, Zhdankin VV. Chem. Rev. 2016; 116: 3328

40 Ivanova MV, Bayle A, Besset T, Poisson T, Pannecoucke X. Angew. Chem. Int. Ed. 2015; 54: 13406

41a Barton DH. R, Finet JP, Khamsia J. Tetrahedron Lett. 1988; 29: 1115
41b Eastman K, Baran PS. Tetrahedron 2009; 65: 3149
41c Phipps RJ, Gaunt MJ. Science 2009; 323: 1593
41d Cahard E, Bremeyer N, Gaunt MJ. Angew. Chem. Int. Ed. 2013; 52: 9284