Direct synthesis of arylketones by nickel-catalyzed addition of arylboronic acids to nitriles

Organic Letters

Volumn 12, Issue 8, 2010, Pages 1736-1739

  Wong, Ying Chieh ^a   Parthasarathy, Kanniyappan ^a   Cheng, Chien Hong ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; KETONE; NICKEL; NITRILE;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

BORONIC ACIDS; CATALYSIS; KETONES; NICKEL; NITRILES;

EID: 77951152090     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1003252     Document Type: Article

References (50)

1. For reviews, see: Tsuji, J. Transition Metal Reagents and Catalysts; Wiley: New York, 2004.
2. Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, Germany, 1998.
3. de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; John Wiley & Sons: Weinheim, Germany, 2004.
4. Hudlicky, M. In Oxidations in Organic Chemistry; ACS Monograph 186; American Chemical Society: Washington, DC, 1990.
5. Larock, R. C. Comprehensive Organic Transformations; VCH: New York, 1989; p 591.
6. Olah, G. Friedel-Crafts and Related Reactions; Interscience Publishers: New York, 1964; Vol. III, p 1259.
7. Osman, M. Helv. Chim. Acta 1982, 65, 2448
8. Zimmerman, H. E.; Paskovich, D. H. J. Am. Chem. Soc. 1964, 86, 2149
9. Heitzler, F. R.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Lehne, V. J. Org. Chem. 1993, 58, 2781
10. Ianni, A.; Waldvogel, S. R. Synthesis 2006, 5, 2103
11. Savari, M. H.; Sharghi, H. J. Org. Chem. 2004, 69, 6953
12. Savari, M. H.; Sharghi, H. Synthesis 2004, 3, 2165
13. Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F. Tetrahedron 2004, 60, 10843
14. Bensari, A.; Zaveri, N. T. Synthesis 2003, 2, 267
15. Ishiyama, T.; Kizaki, H.; Hayashi, T.; Suzuki, A.; Miyaura, N. J. Org. Chem. 1998, 63, 4726
16. Ishiyama, T.; Kizaki, H.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1993, 34, 7595
17. Hirao, T.; Misu, D.; Agawa, T. J. Am. Chem. Soc. 1985, 107, 7179
18. Satoh, T.; Itaya, T.; Miura, M.; Nomura, M. Chem. Lett. 1996, 823
19. Ishiyama, T.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 12043
20. Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260
21. Pucheault, M.; Darses, S.; Genet, J.-P. J. Am. Chem. Soc. 2004, 126, 15356 and references therein
22. Larock, R. C.; Tian, Q.; Pletnev, A. A. J. Am. Chem. Soc. 1999, 121, 3238
23. Pletnev, A. A.; Larock, R. C. Tetrahedron Lett. 2002, 43, 2133
24. Pletnev, A. A.; Tian, Q.; Larock, R. C. J. Org. Chem. 2002, 67, 9276
25. Zhou, C.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 2302
26. Zhou, C.; Larock, R. C. J. Org. Chem. 2006, 71, 3551
27. Zhao, L.; Lu, X. Angew. Chem., Int. Ed. 2002, 41, 4343
28. Zhao, B.; Lu, X. Tetrahedron Lett. 2006, 47, 6765
29. Zhao, B.; Lu, X. Org. Lett. 2006, 8, 5987
30. Ueura, K.; Miyamura, S.; Satoh, T.; Miyaura, M. J. Organomet. Chem. 2000, 595, 31
31. Shimizu, H.; Murakami, M. Chem. Commun. 2007, 2855
32. Kong, K.-C.; Cheng, C.-H. J. Chem. Soc., Chem. Commun. 1991, 423
33. Kong, K.-C.; Cheng, C.-H. Organometallics 1992, 11, 1972
34. Feng, C.-C.; Nandi, M.; Sambaiah, T.; Cheng, C.-H. J. Org. Chem. 1999, 64, 3538
35. Sambaiah, T.; Li, L. P.; Huang, D. J.; Lin, C. H.; Rayabarapu, D. K.; Cheng, C.-H. J. Org. Chem. 1999, 64, 3663
36. Sambaiah, T.; Huang, D. J.; Cheng, C.-H. J. Chem. Soc., Perkin Trans. 1 2000, 195
37. Majumdar, K. K.; Cheng, C.-H. Org. Lett. 2000, 2, 2295
38. Huang, Y.-C.; Majumdar, K. K.; Cheng, C.-H. J. Org. Chem. 2002, 67, 1682
39. Luo, F.-H.; Chu, C.-I.; Cheng, C.-H. Organometallics 1998, 17, 1025
40. Chang, H.-T.; Jeganmohan, M.; Cheng, C.-H. Org. Lett. 2007, 9, 505
41. Hsieh, J.-C.; Cheng, C.-H. Chem. Commun. 2008, 2992
42. Lin, P.-S.; Jeganmohan, M.; Cheng, C.-H Chem. Asian J. 2007, 2, 1409
43. Rayabarapu, D. K.; Cheng, C.-H. Acc. Chem. Res. 2007, 40, 971
44. Lin, P. -S.; Jeganmohan, M.; Cheng, C.-H. Chem. - Eur. J. 2008, 14, 11296
45. Mannathan, S.; Jeganmohan, M.; Cheng, C.-H. Angew. Chem., Int. Ed. 2009, 48, 2192
46. Najera, C.; Sansano, J. M. Angew. Chem., Int. Ed. 2009, 48, 2452
47. Suginome, M.; Yamamoto, A.; Murakami, M. J. Am. Chem. Soc. 2003, 125, 6358
48. Miura, T.; Nakazawa, H.; Murakami, M. Chem. Commun. 2005, 2855
49. Miura, T.; Shimada, M.; Murakami, M. J. Am. Chem. Soc. 2005, 127, 1094
50. Miura, T.; Sasaki, T.; Harumashi, T.; Murakami, M. J. Am. Chem. Soc. 2006, 128, 2516