Ten Years of Adventures with Pd/C Catalysts: From Reductive Processes to Coupling Reactions

François-Xavier Felpin

doi:10.1055/s-0033-1340668

Synlett, Table of Contents

Synlett 2014; 25(08): 1055-1067
DOI: 10.1055/s-0033-1340668

account

Ten Years of Adventures with Pd/C Catalysts: From Reductive Processes to Coupling Reactions

François-Xavier Felpin*

Université de Nantes, UFR Sciences et Techniques, UMR CNRS 6230, CEISAM, 2 rue de la Houssinière, BP 92208, 44322 Nantes 3, France Fax: +33(2)51125402 Email: fx.felpin@univ-nantes.fr

› Author Affiliations

Abstract

All articles of this category

Abstract

This account summarizes ten years of projects in the Felpin group involving Pd/C as a catalyst for cross-coupling reactions. From early studies to recent developments, the story tells of the successes and the failures, and it shows the progress gained in understanding of factors governing the catalytic activity and efficiency of Pd/C catalysts. This account could serve as a textbook for synthetic chemists interested in practical methodologies involving C–C bond formation.

1 Introduction

2 Pd/C: Basic Knowledge

3 Early Studies

4 Homemade Pd/C Catalysts

5 Future Prospects

6 Summary and Outlook

Key words

Pd/C - catalysis - allylic substitution - Suzuki coupling - Heck reaction - arenediazonium salt

Full Text

References

References
1 Felpin F.-X, Landais Y. J. Org. Chem. 2005; 70: 6441

2a Felpin F.-X, Vo-Thanh G, Robins RJ, Villiéras J, Lebreton J. Synlett 2000; 1646
2b Felpin F.-X, Girard S, Vo-Thanh G, Robins RJ, Villiéras J, Lebreton J. J. Org. Chem. 2001; 66: 6305
2c Felpin F.-X, Lebreton J. J. Org. Chem. 2002; 67: 9192
2d Felpin F.-X, Lebreton J. Tetrahedron Lett. 2002; 43: 225

3a Bleicher LS, Cosford ND. P. Synlett 1995; 1115
3b Bleicher LS, Cosford ND. P, Herbaut A, McCallum JS, McDonald IA. J. Org. Chem. 1998; 63: 1109

4a Felpin F.-X, Vo-Thanh G, Villiéras J, Lebreton J. Tetrahedron: Asymmetry 2001; 12: 1121
4b Felpin F.-X, Bertrand M.-J, Lebreton J. Tetrahedron 2002; 58: 7381

For reviews on Pd/C, see:

5a Felpin F.-X, Ayad T, Mitra S. Eur. J. Org. Chem. 2006; 2006: 2679
5b Seki M. Synthesis 2006; 2975
5c Yin L, Liebscher J. Chem. Rev. 2007; 107: 133
5d Pal M. Synlett 2009; 2896

6 Rodríguez-Reinoso F. Carbon 1998; 36: 159
7 For a seminal study, see: Soomro SS, Röhlich C, Köhler K. Adv. Synth. Catal. 2011; 353: 767
8 Lamblin M, Nassar-Hardy L, Hierso JC, Fouquet E, Felpin F.-X. Adv. Synth. Catal. 2010; 352: 33
9 James P, Felpin F.-X, Landais Y, Schenk K. J. Org. Chem. 2005; 70: 7985
10 Kersten L, Taylor RH, Felpin F.-X. Tetrahedron Lett. 2009; 50: 506

For recent general reviews on Suzuki reactions, see:

11a Bellina F, Carpita A, Rossi R. Synthesis 2004; 2419
11b Heravi MM, Hashemi E. Tetrahedron 2012; 68: 9145
11c Han F.-S. Chem. Soc. Rev. 2013; 42: 5270

12 Felpin F.-X. J. Org. Chem. 2005; 70: 8575
13 Felpin F.-X, Lory C, Sow H, Acherar S. Tetrahedron 2007; 63: 3010
14 Lamblin M, Bares H, Dessolin J, Marty C, Bourgougnon N, Felpin F.-X. Eur. J. Org. Chem. 2012; 5525

15a Felpin F.-X, Bourgougnon N, Zanese M. WO 2011070152, 2011
15b Lalut J, Tripoteau L, Marty C, Bares H, Bourgougnon N, Felpin F.-X. Bioorg. Med. Chem. Lett. 2012; 22: 7461

For Pd/C-catalyzed coupling reactions with aryl chlorides, see:

16a LeBlond CR, Andrews AT, Sun Y, Sowa JR. Jr. Org. Lett. 2001; 3: 1555
16b Mukhopadhyay S, Rothenberg G, Joshi A, Baidossi M, Sasson Y. Adv. Synth. Catal. 2002; 344: 348
16c Arvela RK, Leadbetter NE. Org. Lett. 2005; 7: 2101
16d Lyséen M, Köhler K. Synlett 2005; 1671
16e Lyséen M, Köhler K. Synthesis 2006; 692
16f Komáromi A, Novák Z. Chem. Commun. 2008; 4968

17a Darses S, Jeffery T, Genêt J.-P, Brayer J.-L, Demoute J.-P. Tetrahedron Lett. 1996; 37: 3857
17b Darses S, Jeffery T, Brayer J.-L, Demoute J.-P, Genêt J.-P. Bull. Soc. Chim. Fr. 1996; 133: 1095
17c Darses S, Genêt J.-P, Brayer J.-L, Demoute J.-P. Tetrahedron Lett. 1997; 38: 4393
17d Darses S, Michaud G, Genêt J.-P. Tetrahedron Lett. 1998; 39: 5045
17e Brunner H, Le Cousturier de Courcy N, Genêt J.-P. Tetrahedron Lett. 1999; 40: 4815
17f Darses S, Michaud G, Genêt J.-P. Eur. J. Org. Chem. 1999; 1875
17g Brunner H, Le Cousturier de Courcy N, Genêt J.-P. Synlett 2000; 201
17h Darses S, Pucheault M, Genêt J.-P. Eur. J. Org. Chem. 2001; 1121

For recent general reviews on Heck reactions, see:

18a Farina V. Adv. Synth. Catal. 2004; 346: 1553
18b Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
18c Torborg C, Beller M. Adv. Synth. Catal. 2009; 351: 3027
18d Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
18e Muzart J. Tetrahedron 2013; 69: 6735

19 Taylor RH, Felpin F.-X. Org. Lett. 2007; 9: 2911
20 Köhler K, Heidenreich RG, Krauter JG. E, Pietsch J. Chem. Eur. J. 2002; 8: 622
21 Catalyst A: 5% Pd(0)/C-uniform, catalyst B: 5% Pd(0)/C-eggshell, catalyst C: 5% Pd(II)/C-uniform, catalyst D: 5% Pd(II)/C-eggshell.
22 Felpin F.-X, Fouquet E, Zakri C. Adv. Synth. Catal. 2009; 351: 649
23 Felpin, F.-X. unpublished results.
24 Sengupta S, Bhattacharyya S. J. Org. Chem. 1997; 62: 3405

25a Zhao F, Shirai M, Arai M. J. Mol. Catal. A: Chem. 2000; 154: 39
25b Conlon DA, Pipik B, Ferdinand S, LeBlond CR, Sawo JR. Jr, Izzo B, Collins P, Ho G.-J, Williams JM, Shi Y.-J, Sun Y. Adv. Synth. Catal. 2003; 345: 931
25c Chen J.-S, Vasiliev AN, Panarello AP, Khinast JG. Appl. Catal., A 2007; 325: 76
25d Köhler K, Kleist W, Pröckl SS. Inorg. Chem. 2007; 46: 1876
25e Simeone JP, Sowa JR. Jr. Tetrahedron 2007; 63: 12646
25f Köhler K, Heidenreich RG, Soomro SS, Pröckl SS. Adv. Synth. Catal. 2008; 350: 2930
25g Ananikov VP, Beletskaya IP. Organometallics 2012; 31: 1595

26 Davies IW, Matty L, Hughes DL, Reider PJ. J. Am. Chem. Soc. 2001; 123: 10139
27 Felpin F.-X, Fouquet E, Zakri C. Adv. Synth. Catal. 2008; 350: 2559
28 Felpin F.-X, Fouquet E. Chem. Eur. J. 2010; 16: 12440
29 Felpin F.-X, Fouquet E. Synthesis 2011; 2893
30 Phan NT. S, Van Der Sluys M, Jones CW. Adv. Synth. Catal. 2006; 348: 609
31 Rossy C, Fouquet E, Felpin F.-X. Synthesis 2012; 44: 37
32 Felpin F.-X, Miqueu K, Sotiropoulos J.-M, Fouquet E, Ibarguren O, Laudien J. Chem. Eur. J. 2010; 16: 5191

33a Garret CE, Prasad K. Adv. Synth. Catal. 2004; 346: 889
33b Welch CJ, Albaneze-Walker J, Leonard WR, Biba M, DaSilva J, Henderson D, Laing B, Mathre DJ, Spencer S, Bu X, Wang T. Org. Process Res. Dev. 2005; 9: 198

34a Felpin F.-X, Fouquet E. ChemSusChem 2008; 1: 718
34b Climent MJ, Corma A, Iborra S. Chem. Rev. 2011; 111: 1072

35a Felpin F.-X, Ibarguren O, Nassar-Hardy L, Fouquet E. J. Org. Chem. 2009; 74: 1349
35b Felpin F.-X, Coste J, Zakri C, Fouquet E. Chem. Eur. J. 2009; 15: 7238

36 Ibarguren O, Zakri C, Fouquet E, Felpin F.-X. Tetrahedron Lett. 2009; 50: 5071

For claims of a fully heterogeneous mechanism, see ref. 15b and:

37a Maegawa T, Kitamura Y, Sako S, Udzu T, Sakurai A, Tanaka A, Kobayashi Y, Endo K, Bora U, Kurita T, Kozaki A, Monguchi Y, Sajiki H. Chem. Eur. J. 2007; 13: 5937
37b Duplais C, Forman AJ, Baker BA, Lipshutz BH. Chem. Eur. J. 2010; 16: 3366

38 Rossy C, Majimel J, Fouquet E, Delacôte C, Boujtita M, Labrugère C, Tréguer-Delapierre M, Felpin F.-X. Chem. Eur. J. 2013; 19: 14024

For recent general reviews on Sonogashira reactions, see:

39a Doucet H, Hierso J.-C. Angew. Chem. Int. Ed. 2007; 46: 834
39b Chinchilla R, Nájera C. Chem. Rev. 2007; 107: 874