Green and scalable procedure for extremely fast ligandless Suzuki-Miyaura cross-coupling reactions in aqueous IPA using solid-supported Pd in continuous flow

Tetrahedron Letters

Volumn 55, Issue 27, 2014, Pages 3701-3705

  Mateos, Carlos ^a   Rincón, Juan A ^a   Martín Hidalgo, Beatriz ^a,b   Villanueva, José ^a,c  

^a ELI LILLY AND COMPANY   (Spain)

^b Envirohemp   (Spain)

^c ILS Integrated Lab Solutions GmbH   (Germany)

Author keywords

Cross coupling; Flow chemistry; Ligand free catalysis; Scalable process; Supported palladium; Suzuki Miyaura

Indexed keywords

BORONIC ACID DERIVATIVE; HALIDE; PALLADIUM;

ARTICLE; CHEMICAL REACTION; PACKED BED REACTOR; SUZUKI REACTION;

EID: 84902148320     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.05.010     Document Type: Article

References (27)

1. Seminal paper: N. Miyaura, K. Yamada, and A. Suzuki Tetrahedron Lett. 36 1979 3437 3440
2. M.C. Kozlowski, B.J. Morgana, and E.C. Lintona Chem. Soc. Rev. 38 2009 3193 3207
3. N.K. Dmitrii, and A.B. Nikolay Tetrahedron Lett. 47 2006 4225 4229
4. G. Lu, R. Franzén, Q. Zhang, and Y. Xu Tetrahedron Lett. 46 2005 4255 4259
5. H.-U. Blaser, A. Indolese, A. Schnyder, H. Steiner, and M.J. Studer Mol. Cat. A: Chem. 173 2001 3 18
6. Recent Suzuki-Miyaura reactions in aqueous media: H. Liua, B.H. Liua, R. Lia, and H. Chena Tetrahedron Lett. 55 2014 415 418
7. G.A. Edwards, M.A. Trafford, A.E. Hamilton, A.M. Buxton, M.C. Bardeaux, and J.M. Chalker J. Org. Chem. 79 2014 2094 2104
8. C. Liu, X. Rao, Y. Zhang, X. Li, J. Qiu, and Z. Jin Eur. J. Org. Chem. 20 2013 4345 4350
9. For a recent review see: V. Polshettiwar, A. Decottignies, C. Len, and A. Fihri ChemSusChem 3 2010 502 522
10. Y. Kitamura, S. Sako, A. Tsutsui, Y. Monguchi, T. Maegawa, Y. Kitade, and H. Sajikia Adv. Synth. Catal. 352 2010 718 730
11. G. Rothenberg, A.V. Gaikwad, A. Holuigue, M.B. Thathagar, and J.E. ten Elshof Chem. Eur. J. 13 2007 6908 6913
12. J.G. Khinast et al. Appl. Catal. A 325 2007 76 86
13. A. Crowl, and J.F. Louvar Chemical Process Safety: Fundamentals with Applications 2011 Prentice Hall
14. For recent examples of Suzuki cross-couplings in continuous flow using a supported Pd-ligand complex see: J.de M. Muñoz, J. Alcazar, A. de la Hoz, and A. Diaz-Ortiz Adv. Synth. Catal. 354 2012 3456 3460
15. For a review see: T. Nöel, and S.L. Buchwald Chem. Soc. Rev. 40 2011 5010 5029
16. S.G. Newman, and K.F. Jensen Green Chem. 15 2013 1456 1472
17. B.R. Vadula, and M.A. Gonzalez Chem. Today 31 2013 16 20
18. M. Shang, T. Noël, Q. Wang, and V. Hessel Chem. Eng. Technol. 36 2013 1001 1009
19. K. Boodhoo, and A. Harvey Process Intensification Technologies for Green Chemistry: Engineering Solutions for Sustainable Chemical Processing 2013 Wiley-Blackwell
20. M. Damm, T.N. Glasnov, and C.O. Kappe Org. Process Res. Dev. 14 2010 215 224
21. V. Kumar, and K.D.P. Nigam Green Process. Synth. 1 2012 79
22. V. Hessel Chem. Eng. Technol. 32 2009 1655 1681
23. ThalesNano Nanotechnology Inc., Graphisoft Park, H-1031 Budapest, Zahony u.7., Hungary. http://www.ThalesNano.com. Palladium packed bed cartridges are available on various supports: none (Pd black), charcoal (standard and powder type), alumina and silica.
24. The void volume for an H-Cube MIDI cartridge is around 1-1.2 mL (measured experimentally).
25. Estimated residence time is 20 s based on calculated cartridge void volume.
26. For recyclable Pd catalysts in cross-coupling reactions see: R.B. Nasir, and R.S. Varma Chem. Commun. 2013 752
27. S.G. Koenig Scalable Green Chemistry 2013 Pam Standford Publishing