Development of Pd/C-catalyzed cyanation of Aryl halides

Journal of Organic Chemistry

Volumn 76, Issue 2, 2011, Pages 665-668

  Yu, Hannah ^a   Richey, Rachel N ^a   Miller, William D ^a   Xu, Jiansheng ^b   May, Scott A ^a  

^a ELI LILLY AND COMPANY   (United States)

^b Shanghai PharmaExplorer   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL BROMIDES; ARYL CHLORIDE; ARYL HALIDES; CYANATION; PALLADIUM-CATALYZED CYANATION; PRACTICAL METHOD; TO EFFECT;

BROMINE COMPOUNDS; CATALYSIS; CHLORINE COMPOUNDS; PALLADIUM;

METAL HALIDES;

CARBON; HALIDE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYANATION; SUBSTITUTION REACTION;

CATALYSIS; HYDROCARBONS, HALOGENATED; MOLECULAR STRUCTURE; NITRILES; PALLADIUM;

EID: 78651517600     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102037y     Document Type: Article

References (56)

1. Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1989; pp 819 -995.
2. Grundmann, C. In Houben-Weyl: Methoden der organischen Chemie, 4th ed.; Falbe, J., Ed.; Georg Thieme: Stuttgart, Germany, 1985; Vol. E5, pp 1313 -1527.
3. Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances: Syntheses, Patents, Applications, 5th ed.; Georg Thieme: Stuttgart, Germany, 2009.
4. Rappoport, Z. Chemistry of the Cyano Group; John Wiley & Sons: London, UK, 1970.
5. Sandmeyer, T. Ber. Dtsch. Chem. Ges. 1884, 17, 1633
6. Hodgson, H. H. Chem. Rev. 1947, 40, 251
7. Galli, C. Chem. Rev. 1988, 88, 765
8. Mowry, D. T. Chem. Rev. 1948, 42, 189
9. Ellis, G. P.; Romney-Alexander, T. M. Chem. Rev. 1987, 87, 779
10. For reviews, see: Farina, V. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: Oxford, UK, 1995; pp 225 -226.
11. Sundermeier, M.; Zapf, A.; Beller, M. Eur. J. Inorg. Chem. 2003, 3513
12. For representative examples of palladium-catalyzed cyanation of aryl halides, see: Tschaen, D. M.; Desmond, R.; King, A. O.; Fortin, M. C.; Pipik, B.; King, S.; Verhoeven, T. R. Synth. Commun. 1994, 24, 887
13. Anderson, B. A.; Bell, E. C.; Ginah, F. O.; Harn, N. K.; Pagh, L. M.; Wepsiec, J. P. J. Org. Chem. 1998, 63, 8224
14. Maligres, P. E. Tetrahedron Lett. 1999, 40, 8193
15. Jin, F.; Confalone, P. N. Tetrahedron Lett. 2000, 41, 3271
16. Zanon, J.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 2890
17. Sundermeier, M.; Zapf, A.; Mutyala, S.; Baumann, W.; Sans, J.; Weiss, S.; Beller, M. Chem.-Eur. J. 2003, 9, 1828
18. Chidambaram, R. Tetrahedron Lett. 2004, 45, 1441
19. Yang, C.; Williams, J. M. Org. Lett. 2004, 6, 2837
20. Schareina, T.; Zapf, A.; Beller, M. Chem. Commun. 2004, 1388
21. Schareina, T.; Zapf, A.; Beller, M. J. Organomet. Chem. 2004, 689, 4576
22. Stazi, F.; Palmisano, G.; Turconi, M.; Santagostino, M. Tetrahedron Lett. 2005, 46, 1815
23. Schareina, T.; Zapf, A.; Beller, M. Tetrahedron Lett. 2005, 46, 2585
24. Jensen, R. S.; Gajare, A. S.; Toyota, K.; Yoshifuji, M.; Ozawa, F. Tetrahedron Lett. 2005, 46, 8645
25. Hatsuda, M.; Seki, M. Tetrahedron 2005, 61, 9908
26. Weissman, S. A.; Zewge, D.; Chen, C. J. Org. Chem. 2005, 70, 1508
27. Grossman, O.; Gelman, D. Org. Lett. 2006, 8, 1189
28. Pitts, M. R.; McCormack, P.; Whittall, J. Tetrahedron 2006, 62, 4705
29. Littke, A.; Soumeillant, M.; Kaltenback, R. F., III; Cherney, R. J.; Tarby, C. M.; Kiau, S. Org. Lett. 2007, 9, 1711
30. Schareina, T.; Zapf, A.; Magerlein, W.; Muller, N.; Beller, M. Tetrahedron Lett. 2007, 48, 1087
31. Zhu, Y.; Cai, C. Synth. Commun. 2007, 37, 3359
32. Ryberg, P. Org. Process Res. Dev. 2008, 12, 540
33. Ren, Y.; Liu, Z.; He, S.; Zhao, S.; Wang, J.; Niu, R.; Yin, W. Org. Process Res. Dev. 2009, 13, 764
34. Shevlin, M. Tetrahedron Lett. 2010, 51, 4833
35. For representative examples of metal-catalyzed cyanation through C-H functionalization, see: Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790
36. Mariampillai, B.; Alliot, J.; Li, M.; Lautens, M. J. Am. Chem. Soc. 2007, 129, 15372
37. Jia, X.; Yang, D.; Zhang, S.; Cheng, J. Org. Lett. 2009, 11, 4716
38. Kim, J.; Chang, S. J. Am. Chem. Soc. 2010, 132, 10272
39. Sundermeier, M.; Zapf, A.; Beller, M. Angew. Chem., Int. Ed. 2003, 42, 1661
40. Sundermeier, M.; Zapf, A.; Beller., M. Angew. Chem., Int. Ed. 2003, 42, 1661
41. Dobbs, K. D.; Marshall, W. J.; Grushin, V. V. J. Am. Chem. Soc. 2007, 129, 30
42. Erhardt, S.; Grushin, V. V.; Kilpatrick, A. H.; Macgregor, S. A.; Marshall, W. J.; Roe, D. C. J. Am. Chem. Soc. 2008, 130, 4828
43. Marcantonio, K. M.; Frey, L. F.; Liu, Y.; Chen, Y.; Strine, J.; Phenix, B.; Wallace, D. J.; Chen, C. Org. Lett. 2004, 6, 3723
44. Hatsuda, M.; Seki, M. Tetrahedron Lett. 2005, 46, 1849
45. Reactions attempted with higher catalyst loading or using dppf as the ligand also gave little conversion.
46. Seki, M. Synthesis 2006, 2975
47. Yin, L.; Liebscher, J. Chem. Rev. 2007, 107, 133
48. 3P. We found dppf to be superior to other ligands in terms of reactivity and general scope.
49. The reaction did not work when zinc formate was simply replaced with zinc, which suggested additional beneficial effects of zinc formate on the catalyst system. Further investigation is needed to gain additional understanding of the mechanistic effects of zinc formate.
50. Burns, B.; Grigg, R.; Ratananukul, P.; Sridharan, V.; Stevenson, P.; Worakun, T. Tetrahedron Lett. 1988, 29, 4329
51. Ruchirawat, S.; Namsa-aid, A. Tetrahedron Lett. 2001, 42, 1359
52. Kulagowski, J. J.; Curtis, N. R.; Swain, C. J.; Williams, B. J. Org. Lett. 2001, 3, 667
53. Mitchell, D.; Yu, H. Curr. Opin. Discovery Dev. 2003, 6, 876
54. A detection limit of 0.1% was applied.
55. Expensive ligands and higher catalyst loading are often needed for nitrogen-containing heterocycles, see refs 7k, 7r, and 7u.
56. Reproducible results were obtained with all lots of Pd/C tested. Most of the reactions were run with 10 wt % Pd/C purchased from Aldrich (wet, Degussa type E101 NE/W).