Organoborane catalyzed regioselective 1,4-hydroboration of pyridines

Journal of the American Chemical Society

Volumn 137, Issue 15, 2015, Pages 4916-4919

  Fan, Xiaoting ^a   Zheng, Junhao ^a   Li, Zhen Hua ^a   Wang, Huadong ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION INTERMEDIATES; REGIOSELECTIVITY;

DFT CALCULATION; FRUSTRATED LEWIS PAIRS; REGIO-SELECTIVE; TRIFLUOROMETHYL;

PYRIDINE;

BORANE DERIVATIVE; ORGANOBORANE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG; BORON DERIVATIVE;

1,4 HYDROBORATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; HYDROBORATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BORON COMPOUNDS; CATALYSIS; MOLECULAR STRUCTURE; PYRIDINES; STEREOISOMERISM;

EID: 84928485681     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b03147     Document Type: Article

References (55)

1. Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223
2. Lavilla, R. J. Chem. Soc., Perkin Trans. 1 2002, 1141
3. Bull, J. A.; Mousseau, J. J.; Pelletier, G.; Charette, A. B. Chem. Rev. 2012, 112, 2642
4. Edraki, N.; Mehdipour, A. R.; Khoshneviszadeh, M.; Miri, R. Drug Discovery Today 2009, 14, 1058
5. Rueping, M.; Dufour, J.; Schoepke, F. R. Green Chem. 2011, 13, 1084
6. Ouellet, S. G.; Walij, A. M.; MacMillan, D. W. C. Acc. Chem. Res. 2007, 40, 1327
7. Zheng, C.; You, S.-L. Chem. Soc. Rev. 2012, 41, 2498
8. Abril, O.; Whitesides, G. M. J. Am. Chem. Soc. 1982, 104, 1552
9. Wagenknecht, P. S.; Penney, J. M.; Hembre, R. T. Organometallics 2003, 22, 1180
10. Shaw, A. P.; Ryland, B. L.; Franklin, M. J.; Norton, J. R.; Chen, J. Y.-C.; Hall, M. L. J. Org. Chem. 2008, 73, 9668
11. Chen, Q.-A.; Chen, M.-W.; Yu, C.-B.; Shi, L.; Wang, D.-S.; Yang, Y.; Zhou, Y.-G. J. Am. Chem. Soc. 2011, 133, 16432
12. Maenaka, Y.; Suenobu, T.; Fukuzumi, S. J. Am. Chem. Soc. 2012, 134, 367
13. Gutsulyak, D. V.; van der Est, A.; Nikonov, G. I. Angew. Chem., Int. Ed. 2011, 50, 1384
14. Königs, C. D. F.; Klare, H. F. T.; Oestreich, M. Angew. Chem., Int. Ed. 2013, 52, 10076
15. Arrowsmith, M.; Hill, M. S.; Hadlington, T.; Kociok-Köhn, G. Organometallics 2011, 30, 5556
16. Oshima, K.; Ohmura, T.; Suginome, M. J. Am. Chem. Soc. 2012, 134, 3699
17. Dudnik, A. S.; Weidner, V. L.; Motta, A.; Delferro, M.; Marks, T. J. Nat. Chem. 2014, 6, 1100
18. Welch, G. C.; San Juan, R. R.; Masuda, J. D.; Stephan, D. W. Science. 2006, 314, 1124
19. Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46
20. Stephan, D. W.; Erker, G. Chem. Sci. 2014, 5, 2625
21. Stephan, D. W. Org. Biomol. Chem. 2012, 10, 5740
22. Paradies, J. Angew. Chem., Int. Ed. 2014, 53, 3552
23. Hounjet, L.; Stephan, D. W. Org. Process Res. Dev. 2014, 18, 385
24. Feng, X.; Du, H. Tetrahedtron Lett. 2014, 55, 6959
25. Stephan, D. W. Acc. Chem. Res. 2015, 48, 306
26. Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440
27. Blackwell, J. M.; Foster, K. L.; Beck, V. H.; Piers, W. E. J. Org. Chem. 1999, 64, 4887
28. Parks, D. J.; Blackwell, J. M.; Piers, W. E. J. Org. Chem. 2000, 65, 3090
29. Blackwell, J. M.; Sonmor, E. R.; Scoccitti, T.; Piers, W. E. Org. Lett. 2000, 2, 3921
30. Gevorgyan, V.; Ruben, M.; Benson, S.; Liu, J.-X.; Yamamoto, Y. J. Org. Chem. 2000, 65, 6179
31. Rendler, S.; Oesterich, M. Angew. Chem., Int. Ed. 2008, 47, 5997
32. Hermeke, J.; Mewald, M.; Oesterich, M. J. Am. Chem. Soc. 2013, 135, 17537
33. Simonneau, A.; Oesterich, M. Angew. Chem., Int. Ed. 2013, 52, 10076
34. Péres, M.; Hounjet, L. J.; Caputo, C. B.; Dobrovetsky, R.; Stephan, D. W. J. Am. Chem. Soc. 2013, 135, 18308
35. Liu, Y.; Du, H. J. Am. Chem. Soc. 2013, 135, 12968
36. Geier, S. J.; Chase, P. A.; Stephan, D. W. Chem. Commun. 2010, 46, 4884
37. Eisenberger, P.; Bailey, A. M.; Crudden, C. M. J. Am. Chem. Soc. 2012, 134, 17384
38. Erös, G.; Nagy, K.; Mehi, H.; Pápai, I.; Nagy, P.; Király, P.; Tárkányi, G.; Soös, T. Chem.-Eur. J. 2012, 18, 574
39. Mahdi, T.; del Castillo, J. N.; Stephan, D. W. Organometallics 2013, 32, 1971
40. Gandhamsetty, N.; Joung, S.; Park, S.-W.; Park, S.; Chang, S. J. Am. Chem. Soc. 2014, 136, 16780
41. Lu, Z.; Cheng, Z.; Chen, Z.; Weng, L.; Li, Z. H.; Wang, H. Angew. Chem., Int. Ed. 2011, 50, 12227
42. Ye, H.; Lu, Z.; You, D.; Chen, Z.; Li, Z. H.; Wang, H. Angew. Chem., Int. Ed. 2012, 51, 12047
43. Lu, Z.; Wang, Y.; Liu, J.; Lin, Y.-j.; Li, Z. H.; Wang, H. Organometallics 2013, 32, 6753
44. Ashley, A. E.; Herrington, T. T.; Wildgoose, G. G.; Zaher, H.; Thompson, A. L.; Rees, N. H.; Krämer, T.; OHare, D. Chem. Commun. 2008, 4303
45. Dureen, M. A.; Lough, A.; Gilbert, T. M.; Stephan, D. W. J. Am. Chem. Soc. 2011, 133, 14727
46. Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, 194101
47. Zhao, Y.; Truhlar, D. G. J. Chem. Phys. Chem. A 2006, 110, 5121
48. Barbeyon, R.; Benedetti, E.; Cossy, J.; Vasseur, J.-J.; Arseniyadis, S.; Smietana, M. Tetrahedron 2014, 70, 8431
49. Wobser, S. D.; Stephenson, C. J.; Delferro, M.; Marks, T. J. Organometallics 2013, 32, 1317
50. Zhang, Z.; Edkins, R.; Nitsch, J.; Fucke, K.; Steffen, A.; Longobardi, L. E.; Stephan, D. W.; Lambert, C.; Marder, T. B. Chem. Sci. 2015, 6, 308
51. a = 2.84 for 3-bromopyridine for comparison. See: Bjerrum, J.; Schwarzenbach, G.; Sillén, L. G. Stability Constants; Chemical Society: London, 1958.
52. Solé, C.; Fernández, E. Angew. Chem., Int. Ed. 2013, 52, 11351
53. Birch, A.; Karakhanov, E. A. J. Chem. Soc., Chem. Commun. 1975, 480
54. Hantzsch, A. Chem. Ber. 1881, 14, 1637
55. Fowler, F. W. J. Org. Chem. 1972, 37, 1321