Transforming Suzuki-Miyaura cross-couplings of MIDA boronates into a green technology: No organic solvents

Journal of the American Chemical Society

Volumn 135, Issue 47, 2013, Pages 17707-17710

  Isley, Nicholas A ^a   Gallou, Fabrice ^b   Lipshutz, Bruce H ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BORONATES; CROSS-COUPLINGS; GREEN TECHNOLOGY; PRODUCT ISOLATION; ROOM TEMPERATURE; SUZUKI-MIYAURA; SUZUKI-MIYAURA COUPLING;

ORGANIC SOLVENTS;

COUPLINGS;

BORONIC ACID DERIVATIVE; ORGANIC SOLVENT; WATER;

ARTICLE; CHEMICAL REACTION; ROOM TEMPERATURE; STOICHIOMETRY; SUZUKI REACTION; SYNTHESIS; TECHNOLOGY;

BORONIC ACIDS; GREEN CHEMISTRY TECHNOLOGY; IMINO ACIDS; SOLVENTS; WATER;

EID: 84889263077     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja409663q     Document Type: Article

References (43)

1. Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062
2. Torborg, C.; Beller, M. Adv. Synth. Catal. 2009, 351, 3027
3. Hall, D. G. Boronic Acids, 2 nd ed.; Wiley-VCH: Weinheim, Germany, 2011.
4. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457
5. Dunn, P.; Henderson, R.; Mergelsberg, I.; Wells, A. Collaboration to Deliver a Solvent Selection Guide for the Pharmaceutical Industry Moving towards Greener Solvents for Pharmaceutical Manufacturing-An Industry Perspective. ACS GCI Pharmaceutical Roundtable, College Park, Maryland, June 23-25, 2009; ACS: Washington, D.C.; http://acs.confex.com/acs/green09/recordingredirect.cgi/id/ 510.
6. Sheldon, R. A.; Arends, I. W. C. E.; Hanefeld, U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim, Germany, 2007.
7. Amgen Inc., USA, U.S. Patent20,100,273,764, 2010.
8. Abbott Laboratories, USA, PCT Int. Appl.WO 2012129491, 2012.
9. F. Hoffmann-La Roche AG, Switzerland, PCT Int. Appl.WO 2012147518, 2012.
10. Mochida Pharmaceutical Co., Ltd., Japan, PCT Int. Appl.WO 2012147518, 2012; PCT Int. Appl. WO 2012046869, 2012; From PCT Int. Appl. WO 2011078371, 2011.
11. Grob, J. E.; Nunez, J.; Dechantsreiter, M. A.; Hamann, L. G. J. Org. Chem. 2011, 76, 4930
12. Grob, J. E.; Nunez, J.; Dechantsreiter, M. A.; Hamann, L. G. J. Org. Chem. 2011, 76, 10241
13. Grob, J. E.; Dechantsreiter, M. A.; Tichkule, R. B.; Connolly, M. K.; Honda, A.; Tomlinson, R. C.; Hamann, L. G. Org. Lett. 2012, 14, 5578
14. Gillis, E. P.; Burke, M. D. Aldrichimica Acta 2009, 43, 17
15. Knapp, D. M.; Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 2009, 131, 6961
16. Dick, G. R.; Woerly, E. M.; Burke, M. D. Angew. Chem., Int. Ed. 2012, 51, 2667
17. Lipshutz, B. H.; Moser, R.; Voigtritter, K. R. Isr. J. Chem. 2010, 50, 691
18. Burns, A. R.; McAllister, G. D.; Shanahan, S. E.; Taylor, R. J. K. Angew. Chem., Int. Ed. 2010, 49, 5574
19. Fujita, K.; Matsui, R.; Suzuki, T.; Kobayashi, S. Angew. Chem., Int. Ed. 2012, 51, 7271
20. Brak, K.; Ellman, J. A. Org. Lett. 2010, 12, 2004
21. Laird, T. Org. Process Res. Dev. 2012, 16, 1.
22. Dunn, P. J. Pharmaceutical Process Development; Blacker, J. A.; Williams, M. T., Eds.; Royal Society of Chemistry: London, 2011; Chapter 6.
23. Jimenez-Gonzales, C.; Constable, D. J. Green Chemistry and Engineering: A Practical Approach; Wiley: New York, 2011.
24. Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer, J. L.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, T. Y. Green Chem. 2007, 9, 411
25. Bryan, M. C.; Dillon, B.; Hamann, L. G.; Hughes, G. J.; Kopach, M. E.; Peterson, E. A.; Pourashraf, M.; Raheem, I.; Richardson, P. F.; Richter, D. T.; Sneddon, H. F. J. Med. Chem. 2013, 56, 6007
26. Kemeling, G. M. ChemSusChem 2012, 5, 2291
27. Watson, W. J W. Green Chem. 2012, 14, 251
28. Ritter, S. K. Chem. Eng. News 2012, 90 (22), 20.
29. Lipshutz, B. H.; Ghorai, S. Aldrichimica Acta 2012, 45, 3
30. Lipshutz, B. H.; Ghorai, S. Aldrichimica Acta 2008, 41, 59
31. Lipshutz, B. H.; Ghorai, S.; Leong, W. W. Y.; Taft, B. R. J. Org. Chem. 2011, 76, 5061 and references therein
32. Lipshutz, B. H.; Ghorai, S.; Abela, A. R.; Moser, R.; Nishikata, T.; Duplais, C.; Krasovskiy, A. J. Org. Chem. 2011, 76, 4379
33. Lipshutz, B. H.; Isley, N. A.; Fennewald, J. C.; Slack, E. D. Angew. Chem., Int. Ed. 2013, 52, 10592 and references therein
34. Report of MIDA acting as a ligand on palladium: Smith, B. B.; Sawyer, D. T. Inorg. Chem. 1968, 7, 1526
35. Pandarus, V.; Desplantier-Giscard, D.; Gingras, G.; Beland, F.; Ciriminna, R.; Pagliaro, M. Org. Process Res. Dev. 2013, in press, DOI: 10.1021/op400118f.
36. Wexler, R. R.; Greenlee, W. J.; Irvin, J. D.; Goldberg, M. R.; Prendergast, K.; Smith, R. D.; Timmermans, P. B. M. W. M. J. Med. Chem. 1996, 39, 625
37. DeGoey, D. A.; Grampovnik, D. J.; Flentge, C. A.; Flosi, W. J.; Chen, H.-J.; Yeung, C. M.; Randolph, J. T.; Klein, L. L.; Dekhtyar, T.; Colletti, L.; Marsh, K. C.; Stoll, V.; Mamo, M.; Morfitt, D. C.; Nguyen, B.; Schmidt, J. M.; Swanson, S. J.; Mo, H.; Kati, W. M.; Molla, A.; Kempf, D. J. J. Med. Chem. 2009, 52, 2571
38. Aida, W.; Ohtsuki, T.; Li, X.; Ishibashi, M. Tetrahedron 2009, 65, 369
39. Kubota, N. K.; Ohta, E.; Ohta, S.; Koizumi, F.; Suzuki, M.; Ichimura, M.; Ikegami, S. Bioorg. Med. Chem. 2003, 11, 4569
40. Havas, F.; Leygue, N.; Danel, M.; Mestre, B.; Galaup, C.; Picard, C. Tetrahedron 2009, 65, 7673
41. See ref 8 and references therein.
42. Yamamoto, Y.; Takizawa, M.; Yu, X.-Q.; Miyaura, N. Angew. Chem., Int. Ed. 2008, 47, 928
43. Jones, N. A.; Antoon, J. W.; Bowie, A. L.; Borak, J. B.; Stevens, E. P. J. Heterocyclic Chem. 2007, 44, 363