Highly practical synthesis of nitriles and heterocycles from alcohols under mild conditions by aerobic double dehydrogenative catalysis

Organic Letters

Volumn 15, Issue 8, 2013, Pages 1850-1853

  Yin, Weiyu ^a   Wang, Chengming ^a   Huang, Yong ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMMONIA; NITRILE; WATER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALCOHOLS; AMMONIA; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; NITRILES; OXIDATION-REDUCTION; WATER;

EID: 84876569174     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400459y     Document Type: Article

References (49)

1. Friedrich, K.; Wallenfels, K. Chemistry of the Cyano Group; Rappoport, Z., Ed.; Wiley: London, U.K., 1970.
2. Fatiadi, A. J. In Preparation and Synthetic Applications of Cyano Compounds; Wiley: New York, 1983.
3. Miller, J. S.; Manson, J. L. Acc. Chem. Res. 2001, 34, 563
4. Anbarasan, P.; Schareina, T.; Beller, M. Chem. Soc. Rev. 2011, 40, 5049
5. Yan, G.; Yu, J.; Zhang, L. Chin. J. Org. Chem. 2012, 32, 294
6. Schumperli, M. T.; Hammond, C.; Hermans, I. ACS Catal. 2012, 2, 1108
7. Zhang, Y.; Xu, K.; Chen, X.; Hu, T.; Yu, Y.; Zhang, J.; Huang, J. Catal. Commun. 2010, 11, 951
8. Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2003, 42, 1480
9. Enthaler, S. Chem.-Eur. J. 2011, 17, 9316
10. Sueoka, S.; Mitsudome, T.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Chem. Commun. 2010, 46, 8243
11. Zhou, S.; Addis, D.; Das, S.; Junge, K.; Beller, M. Chem. Commun. 2009, 4883
12. Yamaguchi, K.; Fujiwara, H.; Ogasawara, Y.; Kotani, M.; Mizuno, N. Angew. Chem., Int. Ed. 2007, 46, 3922
13. Ishihara, K.; Furuya, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 2002, 41, 2983
14. Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255
15. Yamazaki, S.; Yamazaki, Y. Chem. Lett. 1990, 571
16. McAllister, G. D.; Wilfred, C. D.; Taylor, R. J. K. Synlett 2002, 1291
17. Chen, F.-E.; Li, Y.-Y.; Jia, H.-Q. Synthesis 2002, 1804
18. Iida, S.; Togo, H. Tetrahedron 2007, 63, 8274
19. Mori, N.; Togo, H. Synlett 2005, 1456
20. Iida, S.; Tago, H. Synlett 2007, 407
21. Zhu, C.-J.; Sun, C.-G.; Wei, Y.-Y. Synthesis 2010, 4235
22. Reddy, K. R.; Maheswari, C. U.; Venkateshwar, M.; Prashanthi, S.; Kantam, M. L. Tetrahedron Lett. 2009, 50, 2050
23. Veisi, H. Synthesis 2010, 2631
24. Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062
25. Campbell, A. N.; Stahl, S. S. Acc. Chem. Res. 2012, 45, 851
26. Shi, Z.; Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3381
27. Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3464
28. Martin, A.; Kalevaru, N. V.; Lücke, B.; Sans, J. Green Chem. 2002, 4, 481
29. Denton, W. I.; Bishop, R. B.; Caldwell, H. P.; Chapman, H. D. Ind. Eng. Chem. 1950, 42, 796
30. Ishida, T.; Watanabe, H.; Takei, T.; Hamasaki, A.; Tokunaga, M.; Haruta, M. Appl. Catal. A: Gen. 2012, 425-426, 85
31. Yamaguchi, K.; Kobayashi, H.; Oishi, T.; Mizuno, N. Angew. Chem., Int. Ed. 2012, 51, 544
32. Yamaguchi, K.; He, J.; Oishi, T.; Mizuno, N. Chem.-Eur. J. 2010, 16, 7199
33. Oishi, T.; Kazuya, Y.; Mizuno, N. Angew. Chem., Int. Ed. 2009, 48, 6286
34. Klinkenberg, J. L.; Hartwig, J. F. Angew. Chem., Int. Ed. 2011, 50, 86
35. van der Vlugt, J. I. Chem. Soc. Rev. 2010, 39, 2302
36. Brackman, W.; Gaasbeek, C. J. Recl. Trav. Chim. Pays-Bas. 1966, 85, 257
37. Semmelhack, M. F.; Schmid, C. R.; Cortés, D. A.; Chou, C. S. J. Am. Chem. Soc. 1984, 106, 3374
38. Mannam, S.; Alamsetti, S. K.; Sekar, G. Adv. Synth. Catal. 2007, 349, 2253
39. Figiel, P. J.; Sibaouih, A.; Ahmad, J. U.; Nieger, M.; Räisänen, M. T.; Leskelä, M.; Repo, T. Adv. Synth. Catal. 2009, 351, 2625
40. Hoover, J. M.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 16901
41. Brackman, W.; Smit, P. J. Recl. Trav. Chim. 1963, 82, 757
42. Capdevielle, P.; Lavigne, A.; Maumy, M. Synthesis 1989, 6, 451
43. Juan, M. G. M.; Jennifer, M.; Rosemary, G. C.; Alex, G.; Sabina, C. C.; Chrisine, M. C.; Dario, R. A. Biochem. J. 2009, 421, 29
44. Hoover, J. M.; Ryland, B. L.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 2357
45. Zhou, W.; Zhang, L.-R.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 7094
46. Nasr-Esfahani, M.; Montazerozohori, M.; Mehrizi, S. J. Heterocycl. Chem. 2011, 48, 249
47. Li, X.-N.; Zhou, B.-Y.; Zhang, J.; She, M.-Y.; An, S.-J.; Ge, H.-X.; Li, C.; Yin, B.; Li, J.-L.; Shi, Z. Eur. J. Org. Chem. 2012, 1626
48. McCutcheon, D. C.; Paley, M. A.; Steinhardt, R. C.; Prescher, J. A. J. Am. Chem. Soc. 2012, 134, 7604
49. Ueda, S.; Nagasawa, H. J. Am. Chem. Soc. 2009, 131, 15080