Chelation-assisted palladium-catalyzed direct cyanation of 2-arylpyridine C-H bonds

Organic Letters

Volumn 11, Issue 20, 2009, Pages 4716-4719

  Jia, Xiaofei ^a   Yang, Dongpeng ^a   Zhang, Shouhul ^a   Cheng, Jiang ^a,b  

^a WENZHOU UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CHELATING AGENT; CYANIDE; HYDROGEN; PALLADIUM; PYRIDINE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY;

CARBON; CATALYSIS; CHELATING AGENTS; CYANIDES; HYDROGEN; PALLADIUM; PYRIDINES;

EID: 70349923078     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9017529     Document Type: Article

References (73)

1. (a) Uehling, D. E.; Nanthakumar, S. S.; Groom, D.; Emerson, D. L.; Leitner, P. P.; Luzzio, M.. J.; McIntyre, G.; Morton, B.; Profeta, S.; Sisco, J.; Sternbach, D. D.; Tong, W.-Q.; Vuong, A.; Besterman, J. M. J. Med. Chem. 1995, 38, 1106.
2. (b) Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. Bioore. Med. Chem. 1996, 4, 1379.
3. (c) Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substance: Synthesis, Patents, Applications, 4th ed., Georg Thieme: Stuttgart, 2001.
4. (d) Sundermeier, M.; Zapf, A.; Beller, M.; Sans, S. Tetrahedron Lett. 2001, 42, 6707.
5. (a) Rappoport, Z. The Chemistry of the Cyano Group; Interscience Publishers: London, 1970.
6. (b) Larock, R. C. Comprehensive Organic Transformations; Wiley-VCH: New York, 1988.
7. (a) Schareina, T.; Zapf, A.; Beller, M. Chem. Commun. 2004, 1388.
8. b) Cristau, H.-J.; Ouali, A.; Spindler, J.-F.; Taillefer, M. Chem.-Eur. J. 2005, 11, 2483.
9. (c) Sundermeier, M.; Zapf, A.; Mutyala, S.; Baumann, W.; Sans, J.; Weiss, S.; Beller, M. Chem.-Eur. J. 2003, 9, 1828.
10. (d) Zhu, Y.Z.; Cai, C. Eur. J. Org. Chem. 2007, 2401.
11. (e) Weissman, S. A.; Zewge, D.; Chen, C. Org. Chem. 2005, 70, 1508.
12. (f) Marcantonio, K. M.; Frey, L. F.; Liu, Y.; Chen, Y.; Strine, J.; Phenix, B.; Wallace, D. J.; Chen, C. Org. Lett. 2004, 6, 3723.
13. (g) Yang, C.; Williams, J. M. Org. Lett. 2004, 6, 2867.
14. (h) Littke, A.; Soumeillant, M.; Kaltenbach, R. F., III; Cherney, R. J.; Tarby, C. M.; Kiau, S. Org. Lett. 2007, 9, 1711.
15. (i) Chidambaram, R. Tetrahedron Lett. 2004, 45, 1441.
16. (j) Srivastava, R. R.; Collibee, S. E. Tetrahedron Lett. 2004, 45, 8895.
17. (k) Jin, F.; Confalone, P. N. Tetrahedron Lett. 2000, 41, 3271.
18. Schareina, T.; Zapf, A.; Beller, M. Tetrahedron Lett. 2004, 45, 4576.
19. (m) Sundermeier, M.; Mutyala, S.; Zapf, A.; Spannenberg, A.; Beller, M. J. Organomet. Chem. 2003, 684, 50.
20. (n) Schareina, T.; Zapf, A.; Mägerlein, W.; Müller, N.; Beller, M. Tetrahedron Lett. 2007, 48, 1087.
21. (o) Okano, T.; Iwahara, M.; Kiji, J. Synlett 1998, 243.
22. For representative reviews on C-H functionalization, see: (a) Dyker, G. Handbook of C-H Transformations. Applications in Organic Synthesis; Wjley-VCH: Weinheim, 2005.
23. (b) Murai, S. Activation of Unreactive Bonds and Organic Synthesis; Springer: Berlin, 1999; pp 48-78.
24. (c) Crabtree, R. H. Organomet. Chem. 2004, 689, 4083.
25. (d) Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439.
26. (e) Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 53.18.
27. (f) Kakiuchi, F. Top. Organomet. Chem. 2008, 24, 1.
28. (g) Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013.
29. (h) Goj, L. A.; Gunnoe, T. B. Currr. Org. Chem. 2005, 9, 671.
30. (i) Park, Y. J.;'Park, J. W.; Jun, C. H. Acc. Chem. Res. 2008, 41, 222.
31. j) Li, B.; Yang, S.; Shi, Z. Synlett 2008, 949.
32. (k) Mori, C. A.; Sugie, A. Bull. Chem. Soc. Jpn. 2008, 81, 548.
33. Diaz-Requejo, M. M.; Pérez, P. Chem. Rev. 2008, 108, 3379.
34. (a) Zhang, Y.-H.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 5072.
35. (b) Norinder, J.; Matsumoto, A.; Yoshikai, N.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 5858.
36. (c) Chiong, H. A.; Daugulis, O. Org. Lett. 2007, 9, 1449.
37. (d) Wen, J.; Zhang, J.; Chen, S.-Y.; Li, J.; Yu, X.-Q. Angew. Chem., Int. Ed. 2008, 47, 8897.
38. (e) Wakui, H.; Kawasaki, S.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2004, 126, 8658.
39. (f) Hennessy, E. J.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 12084.
40. (g) Ueda, S.; Nagasawa, H. Angew. Chem., Int. Ed. 2008, 47, 6411.
41. (h) Deng, G. J.; Zhao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2008. 47, 6278.
42. (i) Seregin. I. V.; Ryabova, V.; Gevorgyan, V. J. Am. Chem. Soc 2007, 129, 7742.
43. (j) Kuninobu, Y.; Fujii, Y.; Matsuki, T.; Nishina, Y.; Takai, K. Org. Lett. 2009, 11, 2711.
44. (k.) Reddy, B. V. S.; Reddy, L. R.; Corey, E. Org. Lett. 2006, 8, 3391.
45. Lane, B. S.; Sames, D. Org. Lett. 2004, 6, 2897.
46. (l)Jin, W.W.; Yu, Z.-K.; He, W.; Ye, W.-J.; Xiao, W.-J. Org. Lett. 2009, 11, 1317.
47. (a) Wan, X.; Ma, Z.; Li, B.; Zhang, K.; Cao, S.; Zhang, S.; Shi, Z. J. Am. Chem. Soc. 2006, 128, 7416.
48. (b) Giri. R.; Chen, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 2112.
49. (c) Hull, K. L.; Anani, W. Q.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 7134.
50. (d) Zhao, X.; Dimitrijevias, E.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 3466.
51. (e) Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542.
52. (f) Giri, R.; Liang, J.; Lei, J.-G.; Li, J.-J.; Wang, D.-H.; Chen, X.; Naggar, I. C.; Guo, C.; Foxman, B. M.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 7420.
53. (g) Desai, L. V.; Malik, H. A.; Sanford, M. S. Org. Lett. 2006, 8, 1141.
54. (h) Desai, L. V.; Stowers, K. J.; Sanford, M. S. J. Am. Chem. Soc. 2008, 130, 13285.
55. (i) Thu, H. Y.; Yu, W. Y.; Che, C. M. J. Am. Chem. Soc. 2006, 128, 9048.
56. (j) Li, Z.; Capretto, D. A.; Rahaman, R. O.; He, C. J. Am. Chem. Soc 2007, 129, 12058.
57. (k) Inamoto, K.; Saito, T.; Katsuno, M.; Sakamoto, T.; Hiroya, K. Org. Lett. 2007, 9, 2931.
58. (l) Ihara, H.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 7502.
59. (m) Kawamorita, S.; Ohmiya, H.; Hara, K.; Fukuoka, A.; Sawamura, M. J. Am. Chem. Soc. 2009, 131, 5058.
60. (a) Chen, X.; Hao, X.-S.; Goodhue, C E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790. For the ruthenium-catalyzed cyanation employing NaCN, see:
61. (b) Murahashi, S.-I.; Nakae, T.; Terai, H.; Komiya, N. J. Am. Chem. Soc 2008, 130, 11005.
62. Sundermeier, M.; Zapf, A.; Beller, M. Angew. Chem., Int. Ed. 2003, 42, 1661, and references cited therein.
63. (a) Kalyani, D.; Sanford, M. S. Org. Lett. 2005, 7, 4149.
64. (b) Kalyani, D.; Dick, A. R.; Anani, W. Q.; Sanford, M. S. Org. Lett. 2006, 8, 2523.
65. (a) Dupont, J.; Consorti, C. S.; Spenser, J. Chem. Rev. 2005, 105, 2527.
66. (b) Ryabov, A. D. Synthesis 1985, 233.
67. Yu, W.-Y.; Sit, W. N.; Lai, K.-M.; Zhou, Z.; Chan, A. S. C J. Am Chem. Soc. 2008, 130, 3304.
68. (a) Kunitomo, J.-I.; Satoh, M. Chem. Pharm. Bull. 1982, 30, 2659.
69. b) Kunitomo, J.-I.; Satoh, M.; Shingu, T. Tetrahedron 1983, 39, 3261.
70. (c) Takáni, M.; Takasu, Y.; Takahashi, K. Chem. Pharm. Bull. 1983, 31, 3091.
71. (d) Kunitomo, J.-I.; Kaede, S.; Satoh, M. Chem. Pharm. Bull. 1985, 33, 2778.
72. (e) Hu, S.-M.; Xu, S.-.X.; Yao, X.-S.; Cui, C.-B.; Tezuka, Y.; Kikuchi, T. Chem. Pharm. Bull. 1993, 41, 1866.
73. (f) Yu, B.-W.; Meng, L.-H.; Chen, J.-Y.; Zhou, T.-X.; Cheng, K.-F.; Ding, J.; Qin, G.-W. J. Nat. Prod. 2001, 64, 968.