A general Suzuki cross-coupling reaction of heteroaromatics catalyzed by nanopalladium on amino-functionalized siliceous mesocellular foam

Journal of Organic Chemistry

Volumn 79, Issue 9, 2014, Pages 3946-3954

  Bratt, Emma ^a   Verho, Oscar ^b   Johansson, Magnus J ^a   Bäckvall, Jan Erling ^b  

^a ASTRAZENECA R AND D   (Sweden)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS;

BORONATE ESTERS; HETEROAROMATICS; MESOCELLULAR FOAMS; NANO-CATALYST; NANO-PALLADIUM CATALYSTS; REACTION MIXTURE; SUZUKI CROSS COUPLING REACTIONS; SUZUKI-MIYAURA CROSS-COUPLING REACTION;

CATALYST ACTIVITY;

AROMATIC COMPOUND; BORONIC ACID DERIVATIVE; BROMIDE; CHLORIDE; ESTER; HALIDE; HETEROCYCLIC COMPOUND; IODIDE; NITROGEN; PALLADIUM; POTASSIUM; AMINE; AROMATIC HYDROCARBON; METAL NANOPARTICLE;

ARTICLE; CATALYSIS; FOAM; GREEN CHEMISTRY; LEACHING; NANOCATALYST; REACTION ANALYSIS; SUZUKI REACTION; CHEMICAL STRUCTURE; CHEMISTRY;

AMINES; CATALYSIS; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, AROMATIC; METAL NANOPARTICLES; MOLECULAR STRUCTURE; PALLADIUM;

EID: 84899875427     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500409r     Document Type: Article

References (56)

1. Han, F. Chem. Soc. Rev. 2013, 42, 5270-5298
2. Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722-6737
3. Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168
4. Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451-3479
5. Li, J. J., Ed. Heterocyclic Chemistry in Drug Discovery; Wiley: Hoboken, NJ, 2013; p 697.
6. Hopkin, M. D.; Baxendale, I. R.; Ley, S. V. Org. Biomol. Chem. 2013, 11, 1822-1839
7. Dufert, M. A.; Billingsley, K. L.; Buchwald, S. L. J. Am. Chem. Soc. 2013, 135, 12877-12885
8. Billingsley, K. L.; Anderson, K. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 3484-3488
9. Kudo, N.; Perseghini, M.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1282-1284
10. Ripin, D. H. B.; Bourassa, D. E.; Brandt, T.; Castaldi, M. J.; Frost, H. N.; Hawkins, J.; Johnson, P. J.; Massett, S. S.; Neumann, K.; Phillips, J.; Raggon, J. W.; Rose, P. R.; Rutherford, J. L.; Sitter, B.; Stewart, A. M., III; Vetelino, M. G.; Wei, L. Org. Process Res. Dev. 2005, 9, 440-450
11. Thayer, A. M. Chem. Eng. News 2013, 33, 10-13
12. Guideline for Elemental Impurities: ICH Q3D; ICH, 2013. http://www.ich.org/.
13. Garrett, C. E.; Prasad, K. Adv. Synth. Catal. 2004, 346, 889-900
14. Pagliaro, M.; Pandarus, V.; Ciriminna, R.; Beland, F.; Demma Cara, P. ChemCatChem 2012, 4, 432-445
15. Perez-Lorenzo, M. J. Phys. Chem. Lett. 2012, 3, 167-174
16. Pavia, C.; Ballerini, E.; Bivona, L. A.; Giacalone, F.; Aprile, C.; Vaccaro, L.; Gruttadauria, M. Adv. Synth. Catal. 2013, 355, 2007-2018
17. Yin, L.; Liebscher, J. Chem. Rev. 2007, 107, 133-173
18. Lamblin, M.; Nassar-Hardy, L.; Hierso, J.; Fouquet, E.; Felpin, F. Adv. Synth. Catal. 2010, 352, 33-79
19. Molnar, A. Chem. Rev. 2011, 111, 2251-2320
20. Phan, N. T. S.; Van Der Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609-679
21. Marck, G.; Villiger, A.; Buchecker, R. Tetrahedron Lett. 1994, 35, 3277-3280
22. Felpin, F.; Ayad, T.; Mitra, S. Eur. J. Org. Chem. 2006, 2679-2690
23. Carson, F.; Agrawal, S.; Gustafsson, M.; Bartoszewicz, A.; Moraga, F.; Zou, X.; Martin-Matute, B. Chem.-Eur. J. 2012, 18, 15337-15344
24. Yuan, B.; Pan, Y.; Li, Y.; Yin, B.; Jiang, H. Angew. Chem., Int. Ed. 2010, 49, 4054-4058
25. Gniewek, A.; Ziolkowski, J. J.; Trzeciak, A. M.; Zawadzki, M.; Grabowska, H.; Wrzyszcz, J. J. Catal. 2008, 254, 121-130
26. Lyubimov, S. E.; Vasil'ev, A. A.; Korlyukov, A. A.; Ilyin, M. M.; Pisarev, S. A.; Matveev, V. V.; Chalykh, A. E.; Zlotin, S. G.; Davankov, V. A. React. Funct. Polym. 2009, 69, 755-758
27. Taguchi, A.; Schueth, F. Microporous Mesoporous Mater. 2004, 77, 1-45
28. Wu, S.; Mou, C.; Lin, H. Chem. Soc. Rev. 2013, 42, 3862-3875
29. Ping, E. W.; Pierson, J.; Wallace, R.; Miller, J. T.; Fuller, T. F.; Jones, C. W. Appl. Catal., A 2011, 396, 85-90
30. Ping, E. W.; Wallace, R.; Pierson, J.; Fuller, T. F.; Jones, C. W. Microporous Mesoporous Mater. 2010, 132, 174-180
31. Webb, J. D.; MacQuarrie, S.; McEleney, K.; Crudden, C. M. J. Catal. 2007, 252, 97-109
32. Shakeri, M.; Tai, C.-W.; Göthelid, E.; Oscarsson, S.; Bäckvall, J.-E. Chem.-Eur. J. 2011, 17, 13269-13273
33. Verho, O.; Nagendiran, A.; Johnston, E. V.; Tai, C.-W.; Bäckvall, J.-E. ChemCatChem 2013, 5, 612-618
34. Johnston, E. V.; Verho, O.; Kärkäs, M. D.; Shakeri, M.; Tai, C.-W.; Palmgren, P.; Eriksson, K.; Oscarsson, S.; Bäckvall, J.-E. Chem.-Eur. J. 2012, 18, 12202-12206
35. Verho, O.; Nagendiran, A.; Tai, C.-W.; Johnston, E. V.; Bäckvall, J.-E. ChemCatChem 2014, 6, 205-211
36. Engström, K.; Johnston, E. V.; Verho, O.; Gustafson, K. P. J.; Shakeri, M.; Tai, C.-W.; Bäckvall, J.-E. Angew. Chem., Int. Ed. 2013, 52, 14006-14010
37. a measured in water. Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles: Structure, Reactions, Synthesis, and Applications; Wiley-VCH: Weinheim, Germany, 2013.
38. Prieto, M.; Zurita, E.; Rosa, E.; Munoz, L.; Lloyd-Williams, P.; Giralt, E. J. Org. Chem. 2004, 69, 6812-6820
39. a measured in water. Katrizky, A.; Ramsden, C. A.; Joule, J. A.; Zhdankin, V. V. Handbook of Heterocyclic Chemistry, 3rd ed.; Elsevier: Oxford, U.K., 2010.
40. Sakashita, S.; Takizawa, M.; Sugai, J.; Ito, H.; Yamamoto, Y. Org. Lett. 2013, 15, 4308-4311
41. Yamamoto, Y.; Takizawa, M.; Yu, X.; Miyaura, N. Angew. Chem., Int. Ed. 2008, 47, 928-931
42. Chen, G.; Han, F. Eur. J. Org. Chem. 2012, 2012, 3575-3579
43. Kitamura, Y.; Sako, S.; Tsutsui, A.; Monguchi, Y.; Maegawa, T.; Kitade, Y.; Sajiki, H. Adv. Synth. Catal. 2010, 352, 718-730
44. Siddle, J. S.; Batsanov, A. S.; Caldwell, S. T.; Cooke, G.; Bryce, M. R. Tetrahedron 2010, 66, 6138-6149
45. Dueggeli, M.; Goujon-Ginglinger, C.; Ducotterd, S. R.; Mauron, D.; Bonte, C.; von Zelewsky, A.; Stoeckli-Evans, H.; Neels, A. Org. Biomol. Chem. 2003, 1, 1894-1899
46. Nakamura, T.; Sato, M.; Kakinuma, H.; Miyata, N.; Taniguchi, K.; Bando, K.; Koda, A.; Kameo, K. J. Med. Chem. 2003, 46, 5416-5427
47. McCarthy, A. R.; Hartmann, R. W.; Abell, A. D. Bioorg. Med. Chem. Lett. 2007, 17, 3603-3607
48. Frotscher, M.; Ziegler, E.; Marchais-Oberwinkler, S.; Kruchten, P.; Neugebauer, A.; Fetzer, L.; Scherer, C.; Mueller-Vieira, U.; Messinger, J.; Thole, H.; Hartmann, R. W. J. Med. Chem. 2008, 51, 2158-2169
49. Bamborough, P.; Diallo, H.; Goodacre, J. D.; Gordon, L.; Lewis, A.; Seal, J. T.; Wilson, D. M.; Woodrow, M. D.; Chung, C. J. Med. Chem. 2012, 55, 587-596
50. Guram, A. S.; Wang, X.; Bunel, E. E.; Faul, M. M.; Larsen, R. D.; Martinelli, M. J. J. Org. Chem. 2007, 72, 5104-5112
51. Molander, G. A.; Trice, S. L. J.; Kennedy, S. M. J. Org. Chem. 2012, 77, 8678-8688
52. Su, W.; Urgaonkar, S.; McLaughlin, P. A.; Verkade, J. G. J. Am. Chem. Soc. 2004, 126, 16433-16439
53. Mullens, P. R. Tetrahedron Lett. 2009, 50, 6783-6786
54. Li, J.; Deng, C.; Xie, Y. Synth. Commun. 2007, 37, 2433-2448
55. Kumar, M. R.; Park, K.; Lee, S. Adv. Synth. Catal. 2010, 352, 3255-3266
56. Lipshutz, B. H.; Abela, A. R. Org. Lett. 2008, 10, 5329-5332