A general palladium catalyst system for suzuki-miyaura coupling of potassium aryltrifluoroborates and aryl mesylates

Journal of Organic Chemistry

Volumn 75, Issue 15, 2010, Pages 5109-5112

  Chow, Wing Kin ^a   So, Chau Ming ^a   Lau, Chak Po ^a   Kwong, Fuk Yee ^a  

^a HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS COUPLING REACTIONS; MESYLATES; PALLADIUM CATALYST; SUZUKI-MIYAURA COUPLING; SUZUKI-TYPE CROSS-COUPLING;

CATALYSTS; HYDROCARBONS; PALLADIUM;

CHEMICAL REACTIONS;

ALKYL GROUP; BORIC ACID; FLUORINE DERIVATIVE; HETEROCYCLIC COMPOUND; MESYLIC ACID DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; REACTION ANALYSIS; SUZUKI REACTION;

EID: 77955165445     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100846t     Document Type: Article

References (68)

1. For reviews, see: Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4442
2. Nicolaou, K. C.; Sorensen, E. J. Classic in Total Synthesis II, More Targets, Strategies and Methods; Wiley-VCH: Weinheim, Germany, 2003.
3. de Meijere, A.; Diederich, F., Ed. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2004; Vols. 1-2.
4. Beller, M.; Bolm, C. Transition Metals for Organic Synthesis, Building Blocks and Fine Chemicals, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2004; Vols. 1-2.
5. Nigeshi, E., Ed. Handbook of Organopalladium for Organic Synthesis; Wiley-Interscience: Weinheim, Germany, 2002; Vols. 1-2.
6. Tsuji, J. Palladium Reagents and Catalysts, 2nd ed.; Wiley: Chichester, UK, 2004.
7. Yin, L. X.; Liebscher, J. Chem. Rev. 2007, 107, 133
8. Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651
9. Roglans, A.; Pla-Quintana, A.; Moreno-Manas, M. Chem. Rev. 2006, 106, 4622
10. Kwong, F. Y.; Chan, A. S. C. Synlett 2008, 1440
11. Ackermann, L., Modern Arylation Methods; Wiley-VCH: Weinheim, Germany, 2009.
12. King, A. O.; Yasuda, N. In Organometallics in Process Chemistry; Larsen, R. D., Ed.; Springer-Verlag: Berlin, Germany, 2004; pp 205 - 245.
13. Miyaura, N. Top. Curr. Chem. 2002, 219, 11
14. Suzuki, A. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 53 - 106.
15. Suzuki, A. J. Organomet. Chem. 2002, 653, 54
16. Hall, D. G., Boronic Acids; Wiley-VCH: Weinheim, Germany, 2006.
17. 3K salts, see: Molander, G. A.; Canturk, B. Angew. Chem., Int. Ed. 2009, 48, 9240
18. Molander, G. A.; Ellis, N. O. Acc. Chem. Res. 2007, 40, 275
19. For selected examples, see: Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3020-3027
20. Molander, G. A.; Cooper, D. J. J. Org. Chem. 2007, 72, 3558
21. Molander, G. A.; Ham, J.; Canturk, B. Org. Lett. 2007, 9, 821
22. For recent selected examples from Molanders group, see: Molander, G. A.; Cavalcanti, L. N.; Canturk, B.; Pan, P. S.; Kennedy, L. E. J. Org. Chem. 2009, 74, 7364
23. Cho, Y. A.; Kim, D. S.; Ahn, H. R.; Canturk, B.; Molander, G. A.; Ham, J. Org. Lett. 2009, 11, 4330
24. Molander, G. A.; Febo-Ayala, W.; Jean-Gerard, L. Org. Lett. 2009, 11, 3830
25. Molander, G. A.; Jean-Gerard, L. J. Org. Chem. 2009, 74, 5446
26. Dreher, S. D.; Lim, S. E.; Sandrock, D. L.; Molander, G. A. J. Org. Chem. 2009, 74, 3626
27. Molander, G. A.; Jean-Gerard, L. J. Org. Chem. 2009, 74, 1297
28. Molander, G. A.; Cooper, D. J. J. Org. Chem. 2008, 73, 3885
29. Molander, G. A.; Gormisky, P. E.; Sandrock, D. L. J. Org. Chem. 2008, 73, 2052
30. Molander, G. A.; Gormisky, P. E. J. Org. Chem. 2008, 73, 7481
31. Molander, G. A.; Sandrock, D. L. Org. Lett. 2007, 9, 1597
32. Molander, G. A.; Vargas, F. Org. Lett. 2007, 9, 203
33. Barder, T. E.; Buchwald, S. L. Org. Lett. 2004, 6, 2649
34. For recent selected examples, see: Abel, R.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2009, 48, 6289
35. Doucet, H. Eur. J. Org. Chem. 2008, 2013
36. Kabalka, G. W.; Zhou, L.-L.; Naravane, A. Tetrahedron Lett. 2006, 47, 6887
37. Harker, R. L.; Crouch, R. D. Synthesis 2007, 25
38. Wu, J.; Zhang, L.; Luo, Y. Tetrahedron Lett. 2006, 47, 6747
39. Wu, J.; Zhang, L.; Xia, H.-G. Tetrahedron Lett. 2006, 47, 1525
40. Cella, R.; Cunha, R. L. O. R.; Reis, A. E. S.; Pimenta, D. C.; Klitzke, C. F.; Stefani, H. A. J. Org. Chem. 2006, 71, 244
41. Kabalka, G. W.; Al-Masum, M. Tetrahedron Lett. 2005, 46, 6329
42. Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 4397
43. Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 1381
44. Fang, G.-H.; Yan, Z.-J.; Deng, M.-Z. Org. Lett. 2004, 6, 357
45. Darses, S.; Genet, J.-P. Eur. J. Org. Chem. 2003, 4313
46. Arvela, R. K.; Leadbeater, N. E.; Mack, T. L.; Kormos, C. M. Tetrahedron Lett. 2006, 47, 217
47. For a review describing indolyl/imidazolyl phosphine ligands, see: Zapf, A.; Beller, M. Chem. Commun. 2005, 431
48. For our recent developments of indolyl phosphine, see: So, C. M.; Yeung, C. C.; Lau, C. P.; Kwong, F. Y. J. Org. Chem. 2008, 73, 7803
49. 2O, ca. $5/g, from commercial suppliers in 2005-2006.
50. For Ni-catalyzed mesylate coupling reactions, see: Percec, V.; Bae, J.-Y.; Zhao, M.; Hill, D. H. J. Org. Chem. 1995, 60, 176
51. Percec, V.; Bae, J.-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 1060
52. Percec, V.; Golding, G. M.; Smidrkal, J.; Weichold, O. J. Org. Chem. 2004, 69, 3447
53. For Pd-catalyzed mesylate coupling reactions, see: Fors, B. P.; Watson, D. A.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 13552
54. Zhang, L.; Qing, J.; Yang, P.; Wu, J. Org. Lett. 2008, 10, 4971
55. So, C. M.; Zhou, Z.; Lau, C. P.; Kwong, F. Y. Angew. Chem., Int. Ed. 2008, 47, 6402
56. So, C. M.; Lee, H. W.; Lau, C. P.; Kwong, F. Y. Org. Lett. 2009, 11, 317
57. Naber, J. R.; Fors, B. P.; Wu, X.; Gunn, J. T.; Buchwald, S. L. Heterocycles 2010, 80, 1215
58. See refs 14 and 15.
59. a = -14.9).
60. For Ni-catalyzed Suzuki-type coupling with tosylate partners, see: Zim, D.; Lando, V. R.; Dupont, J.; Monteiro, A. L. Org. Lett. 2001, 3, 3049
61. Tang, Z. Y.; Hu, Q. S. J. Am. Chem. Soc. 2004, 126, 3058
62. For Pd-catalyzed Suzuki-type coupling with tosylate partners, see: Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818
63. Zhang, L.; Meng, T.; Wu, J. J. Org. Chem. 2007, 72, 9346
64. So, C. M.; Lau, C. P.; Chan, A. S. C.; Kwong, F. Y. J. Org. Chem. 2008, 73, 7731
65. 3K was reported.
66. For an effective system reported by Buchwald and co-workers focusing on heteroaryl couplings, see: Bhayana, B.; Fors, B. P.; Buchwald, S. L. Org. Lett. 2009, 11, 3954
67. Eicher, T.; Hauptmann, S. The Chemistry of Heterocycles, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2003.
68. Molander, G. A.; Canturk, B.; Kennedy, L. E. S. J. Org. Chem. 2009, 74, 973