Copolymer-incarcerated nickel nanoparticles with N-heterocyclic carbene precursors as active cross-linking agents for Corriu-Kumada-Tamao reaction

Journal of the American Chemical Society

Volumn 135, Issue 29, 2013, Pages 10602-10605

  Soulé, Jean François ^a   Miyamura, Hiroyuki ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS COUPLING REACTIONS; CROSS LINKING AGENTS; FIELD GRADIENT; MAGIC ANGLE SPINNING NMR; MATRIX STRUCTURE; N-HETEROCYCLIC CARBENES; NICKEL NANOPARTICLES; POLYMER SUPPORTS;

CATALYSTS; CROSSLINKING; FUNCTIONAL GROUPS; LIGANDS; MAGIC ANGLE SPINNING; NANOPARTICLES;

NICKEL;

CARBENE; COPOLYMER; HETEROCYCLIC COMPOUND; N HETEROCYCLIC CARBENE; NANOPARTICLE; NICKEL; NICKEL NANOPARTICLE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CORRIU KUMADA TAMAO REACTION; CROSS LINKING; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 84880832768     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja404006w     Document Type: Article

References (55)

1. Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417
2. Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062
3. Astruc, D.; Lu, F.; Aranzaes, J. R. Angew. Chem., Int. Ed. 2005, 44, 7852
4. Polshettiwar, V.; Basset, J.-M.; Astruc, D. Chemsuschem 2012, 5, 6
5. Djakovitch, L.; Koehler, K. J. Am. Chem. Soc. 2001, 123, 5990
6. Reetz, M. T.; Westermann, E. Angew. Chem., Int. Ed. 2000, 39, 165
7. Astruc, D. Inorg. Chem. 2007, 46, 1884
8. Corriu, R. J. P.; Masse, J. P. J. Chem. Soc., Chem. Commun. 1972, 0, 144a
9. Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374
10. Wang, Z.-X.; Liu, N. Eur. J. Inorg. Chem. 2012, 901
11. Phapale, V. B.; Cardenas, D. J. Chem. Soc. Rev. 2009, 38, 1598
12. Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.-M.; Garg, N. K.; Percec, V. Chem. Rev. 2010, 111, 1346
13. Chen, X.; Wang, L.; Liu, J. Synthesis 2009, 2009, 2408
14. Lipshutz, B. H.; Blomgren, P. A. J. Am. Chem. Soc. 1999, 121, 5819
15. Lipshutz, B. H.; Tomioka, T.; Blomgren, P. A.; Sclafani, J. A. Inorg. Chim. Acta 1999, 296, 164
16. Lipshutz, B. H.; Sclafani, J. A.; Blomgren, P. A. Tetrahedron 2000, 56, 2139
17. Tasler, S.; Lipshutz, B. H. J. Org. Chem. 2002, 68, 1190
18. Phan, N. T. S.; Brown, D. H.; Styring, P. Green Chem. 2004, 6, 526
19. Alonso, F.; Riente, P.; Yus, M. Acc. Chem. Res. 2011, 44, 379
20. Lipshutz, B. H.; Ueda, H. Angew. Chem., Int. Ed. 2000, 39, 4492
21. Lipshutz, B. H.; Tasler, S. Adv. Synth. Catal. 2001, 343, 327
22. Lipshutz, B. H.; Frieman, B. A.; Lee, C.-T.; Lower, A.; Nihan, D. M.; Taft, B. R. Chem. Asian J. 2006, 1, 417
23. Akiyama, R.; Kobayashi, S. Chem. Rev. 2009, 109, 594
24. Kobayashi, S.; Miyamura, H. Chem. Rec. 2010, 10, 271
25. Miyamura, H.; Matsubara, R.; Miyazaki, Y.; Kobayashi, S. Angew. Chem., Int. Ed. 2007, 46, 4151
26. Soulé, J.-F.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc. 2011, 133, 18550
27. Soulé, J.-F.; Miyamura, H.; Kobayashi, S. Asian J. Org. Chem. 2012, 1, 319
28. Soulé, J.-F.; Miyamura, H.; Kobayashi, S. Chem. Commun. 2013, 49, 355
29. Miyamura, H.; Shiramizu, M.; Matsubara, R.; Kobayashi, S. Chem. Lett. 2008, 37, 360
30. Yuan, H.; Yoo, W.-J.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc. 2012, 134, 13970
31. Yasukawa, T.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc. 2012, 134, 16963
32. Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122
33. Díez-González, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874
34. Poyatos, M.; Mata, J. A.; Peris, E. Chem. Rev. 2009, 109, 3677
35. Schuster, O.; Yang, L.; Raubenheimer, H. G.; Albrecht, M. Chem. Rev. 2009, 109, 3445
36. Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 6940
37. Vignolle, J.; Tilley, T. D. Chem. Commun. 2009, 0, 7230
38. Lara, P.; Rivada-Wheelaghan, O.; Conejero, S.; Poteau, R.; Philippot, K.; Chaudret, B. Angew. Chem., Int. Ed. 2011, 50, 12080
39. Gonzalez-Galvez, D.; Lara, P.; Rivada-Wheelaghan, O.; Conejero, S.; Chaudret, B.; Philippot, K.; van Leeuwen, P. W. N. M. Catal. Sci. Technol. 2013, 3, 99
40. Ranganath, K. V. S.; Kloesges, J.; Schäfer, A. H.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 7786
41. Tennyson, A. G.; Lynch, V. M.; Bielawski, C. W. J. Am. Chem. Soc. 2010, 132, 9420
42. Joshi-Pangu, A.; Wang, C.-Y.; Biscoe, M. R. J. Am. Chem. Soc. 2011, 133, 8478
43. Mitsudo, K.; Doi, Y.; Sakamoto, S.; Murakami, H.; Mandai, H.; Suga, S. Chem. Lett. 2011, 40, 936
44. Zhing, K.; Conda-Sheridan, M.; Cooke, S. R.; Louie, J. Organometallics 2011, 30, 2546
45. Iglesias, M. J.; Prieto, A.; Nicasio, M. C. Org. Lett. 2012, 14, 4318
46. Kremzow, D.; Seidel, G.; Lehmann, C. W.; Fürstner, A. Chem.-Eur. J. 2005, 11, 1833
47. Bönnemann, H.; Brijoux, W.; Joussen, T. Angew. Chem., Int. Ed. 1990, 29, 273
48. For an example of SR-MAS analysis, see: Kobayashi, S.; Akiyama, R.; Furuta, T.; Moriwaki, M. Molecules 1998, 2, 35
49. Mu, X.-d.; Meng, J.-q.; Li, Z.-C.; Kou, Y. J. Am. Chem. Soc. 2005, 127, 9694
50. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033
51. Yoshikai, N.; Matsuda, H.; Nakamura, E. J. Am. Chem. Soc. 2009, 131, 9590
52. Jin, Z.; Li, Y.-J.; Ma, Y.-Q.; Qiu, L.-L.; Fang, J.-X. Chem.-Eur. J. 2012, 18, 446
53. Manolikakes, G.; Knochel, P. Angew. Chem., Int. Ed. 2009, 48, 205
54. Martin, R.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3844
55. Vechorkin, O.; Proust, V.; Hu, X. J. Am. Chem. Soc. 2009, 131, 9756