Palladium-catalyzed preparation of Weinreb amides from boronic acids and N-methyl-N-methoxycarbamoyl chloride

Journal of Organic Chemistry

Volumn 75, Issue 4, 2010, Pages 1251-1258

  Krishnamoorthy, Ravi ^a   Lam, Sang Q ^a   Manley, Christopher M ^a   Herr, R Jason ^a  

^a ALBANY MOLECULAR RESEARCH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZAMIDES; BORONIC ACID; CHEMICAL EQUATIONS; METHOXY; ORGANOBORONIC ACIDS; PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS; SIMPLE PROTOCOL; WEINREB AMIDES;

ACIDS; AMIDES; CHEMICAL BONDS; CHLORINE COMPOUNDS; PALLADIUM; POTASSIUM;

SYNTHESIS (CHEMICAL);

AMIDE; BENZAMIDE DERIVATIVE; BORONIC ACID DERIVATIVE; CARBAMIC ACID DERIVATIVE; FLUORINE DERIVATIVE; PALLADIUM; POTASSIUM DERIVATIVE;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

ALKENES; AMIDES; BORONIC ACIDS; CARBAMATES; CATALYSIS; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77249134097     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902647h     Document Type: Article

References (60)

1. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
2. For reviews, see: (a) Balasubramaniam, S.; Aidhen, I. S. Synthesis 2008, 23, 3707.
3. (b) Khlestkin, V. K.; Mazhukin, D. G. Curr. Org. Chem. 2003, 7, 967.
4. (c) Singh, J.; Satyamurthi, N.; Aidhen, I. S. J. Prakt. Chem. 2000, 342, 340.
5. (d) Mentzel, M.; Hoffmann,H.M.R. J. Prakt. Chem. 1997, 339, 517.
6. (e) Sibi, M. P. Org. Prep. Proced. Int. 1993, 25, 15.
7. For examples, see: (a) Woo, J. C. S.; Fenster, E.; Dake, G. R. J. Org. Chem. 2004, 69, 8984.
8. (b) Hioki, K.; Kobayashi, H.; Ohkihara, R.; Tani, S.; Kunishima, M. Chem. Pharm. Bull. 2004, 52, 470.
9. (c) Kim, M.; Lee, H.; Han, K.-J.; Kay, K.-Y. Synth. Commun. 2003, 33, 4013.
10. (d) Colobert, F. C.; Des Mazery, R.; Solladié, G.; Carreño, M. C. Org. Lett. 2002, 4, 1723.
11. (e) De Luca, L.; Giacomelli, G.; Taddei, M. J. Org. Chem. 2001, 66, 2534.
12. (f) Bailén, M. A.; Chinchilla, R.; Dodsworth, D. J.;Nájera, C. Tetrahedron Lett. 2001, 42, 5013.
13. (g) Banwell, M.; Smith, J. Synth. Commun. 2001, 31, 2011.
14. (h) Tunoori, A. R.; White, J. M.; Georg, G. I. Org. Lett. 2000, 2, 4091.
15. (i) Gibson, C. L.; Hanada, S. Tetrahedron: Asymmetry 1996, 7, 1281.
16. (j) Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461.
17. (k) Einhorn, J.; Einhorn, C.; Luche, J.-L. Synth. Commun. 1990, 20, 1105.
18. (a) Martinelli, J. R.; Watson, D. A.; Freckmann, D. M. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2008, 73, 7102.
19. (b) Martinelli, J. R.; Freckmann, D. M. M.; Buchwald, S. L. Org. Lett. 2006, 8, 4843.
20. (c) Zhuang, L.; Wai, J. S.; Embrey, M. W.; Fisher, T. E.; Egbertson, M. S.; Payne, L. S.; Guare, J. P. Jr.; Vacca, J. P.; Hazuda, D. J.; Felock, P. J.; Wolfe, A. L.; Stillmock, K. A.; Witmer,M. V.; Moyer, G.; Schleif, W. A.; Gabryelski, L. J.; Leonard, Y. M.; Lynch, J. J. Jr.; Michelson, S. R.; Young, S. D. J. Med. Chem. 2003, 46, 453.
21. (a) Deagostino, A.; Larini, P.; Occhiato, E. G.; Pizzuto, L.; Prandi, C.; Venturello, P. J. Org. Chem. 2008, 73, 1941.
22. (b) Aungst, R. A.; Funk, R. L. J. Am. Chem. Soc. 2001, 123, 9455.
23. Murakami, M.; Hoshino, Y.; Ito, H.; Ito, Y. Chem. Lett. 1998, 2, 163.
24. For preparations of Weinreb amides reacting N-methoxy-N-methylcarbamoyl chloride with organolithium or organomagnesium reagents, see: (a) Lee, J. I. Bull. Korean Chem. Soc. 2007, 28, 695.
25. (b) Lee, J. I.; Jung, H. J. Korean Chem. Soc. 2005, 49, 609.
26. (c) Lee, J. I.; Park, H. Bull. Korean Chem. Soc. 2002, 23, 521.
27. (d) Tius, M. A.; Busch-Petersen, J.; Yamashita, M. Tetrahedron Lett. 1998, 39, 4219.
28. Duan, Y.-Z.; Deng, M.-Z. Synlett 2005, 2, 355.
29. Lysén, M.; Kelleher, S.; Begtrup, M.; Kristensen, J. L. J. Org. Chem. 2005, 70, 5342.
30. For other examples of metal-catalyzed cross-coupling reactions utilizing N-methoxy-N-methylcarbamoyl chloride, see ref 5 and: (a) Sato, Y.; Tamura, T.; Kinbara, A.; Miwako, M. Adv. Synth. Catal. 2007, 349, 647.
31. (b) Sato, Y.; Tamura, T.; Mori, M. Angew. Chem., Int. Ed. 2004, 43, 2436.
32. For instances involving heterolytic cleavage of N-alkoxyamide nitrogen-oxygen bonds of Weinreb amides under some cross-coupling conditions, see: (a) Odell, L. R.; Sävmarker, J.; Larhed, M. Tetrahedron Lett. 2008, 49, 6115.
33. (b) Zhang, Z.; Yu, Y.; Liebeskind, L. S. Org. Lett. 2008, 10, 3005.
34. (a) Urawa, Y.; Ogura, K. Tetrahedron Lett. 2003, 44, 271.
35. (b) Urawa, Y.; Naka, H.; Miyazawa, M.; Souda, S.; Ogura, K. J. Organomet. Chem. 2002, 653, 269.
36. Fu, X.-L.; Wu, L.-L.; Fu, H.-Y.; Chen, H.; Li, R.-X. Eur. J. Org. Chem. 2009, 2051 and references cited therein.
37. A report recently appeared describing the palladium(II)-catalyzed addition of two arylboronic acids to alkynyl Weinreb amides to provide trisubstituted α,β-unsaturated Weinreb amide products: Bush, A. G.; Jiang, J. L.; Payne, P. R.; Ogilvie, W. W. Tetrahedron 2009, 65, 8502.
38. For articles and reviews citing work with potassium organotrifluoroborates, see: (a) Molander, G. A.; Canturk, B.; Kennedy, L. E. J. Org. Chem. 2009, 74, 973.
39. (b) Darses, S.; Genet, J.-P. Chem. Rev. 2008, 108, 288.
40. (c) Stefani, H. A.; Cella, R.; Adriano, S. Tetrahedron 2007, 63, 3623.
41. (d) Molander, G. A.; Ellis, N. Acc. Chem. Res. 2007, 40, 275.
42. (a) Lucas, S.; Heim, R.; Negri, M.; Antes, I.; Ries, C.; Schewe, K. E.; Bisi, A.; Gobbi, S.; Hartmann, R. W. J. Med. Chem. 2008, 51, 6138.
43. (b) Bourne, C.; Roy, S.; Wiley, J. L.; Martin, B. R.; Thomas, B. F.; Mahadevan, A.; Razdan, R. K. Bioorg. Med. Chem. 2007, 15, 7850.
44. (c) Lee, J. I. Bull. Korean Chem. Soc. 2007, 28, 695.
45. (d) Sofikiti, N.; Tofi, M.; Montagnon, T.; Vassilikogiannakis, G.; Stratakis, M. Org. Lett. 2005, 7, 2357.
46. (a) Murphy, J. A.; Commeureuc, A. G. J.; Snaddon, T. N.; McGuire, T. M.; Khan, T. A.; Hisler, K.; Dewis, M. L.; Carling, R. Org. Lett. 2005, 7, 1427.
47. (b) Kokotos, C. G.; Baskakis, C.; Kokotos, G. J. Org. Chem. 2008, 73, 8623.
48. (c) Pippel, D. J.; Mapes, C. M.; Mani, N. S. J. Org. Chem. 2007, 72, 5828.
49. (d) Bariau, A.; Canet, J.-L.; Chalard, P.; Troin, Y. Tetrahedron: Asymmetry 2005, 16, 3650.
50. Mani, N. S.; Jablonowski, J. A.; Jones, T. K. J. Org. Chem. 2004, 69, 8115.
51. (a) Liverton, N. J.; Butcher, J. W.; Claiborne,C. F.; Claremon, D. A.; Libby, B. E.; Nguyen, K. T.; Pitzenberger, S. M.; Selnick, H. G.; Smith, G. R.; Tebben, A.; Vacca, J. P.; Varga, S. L.; Agarwal, L.; Dancheck, K.; Forsyth, A. J.; Fletcher, D. S.; Frantz, B.; Hanlon, W. A.; Harper, C. F.; Hofsess, S. J.; Kostura, M.; Lin, J.; Luell, S.; O'Neill, E. A.; Orevillo, C. J.; Pang, M.; Parsons, J.; Rolando, A.; Sahly, Y.; Visco, D. M.; O'Keefe, S. J. J. Med. Chem. 1999, 42, 2180.
52. (b) Gallagher, T. F.; Seibel, G. L.; Kassis, S.; Laydon, J. T.; Blumenthal, M. J.; Lee, J. C.; Lee, D.; Boehm, J. C.; Fier-Thompson, S. M.; Abt, J. W.; Soreson, M. E.; Smietana, J. M.; Hall, R. F.; Garigipati, R. S.; Bender, P. E.; Erhard, K. F.; Krog, A. J.; Hofmann, G. A.; Sheldrake, P. L.; McDonnell, P. C.; Kumar, S.; Young, P. R.; Adams, J. L. Bioorg. Med. Chem. 1997, 5, 49.
53. (a) Matsuo, J.-I.; Aizawa, Y. Chem. Commun. 2005, 18, 2399.
54. (b) Fry, A. J.; Rho, A. K.; Sherman, L. R.; Sherwin, C. S. J. Org. Chem. 1991, 56, 3283.
55. (a) Kokotos, C. G.; Baskakis, C.; Kokotos, G. J. Org. Chem. 2008, 73, 8623.
56. (b) Pippel, D. J.; Mapes, C. M.; Mani, N. S. J. Org. Chem. 2007, 72, 5828.
57. (c) Bariau, A.; Canet, J.-L.; Chalard, P.; Troin, Y. Tetrahedron: Asymmetry 2005, 16, 3650.
58. Shintani, R.; Kimura, T.; Hayashi, T. Chem. Commun. 2005, 25, 3213.
59. (a) Boyd, R. E.; Rasmussen, C. R.; Press, J. B.; Raffa, R. B.; Codd, E. E.; Connelly, C. D.; Li, Q. S.; Martinez, R. P.; Lewis, M. A.; Almond, H. R.; Reitz, A. B. J. Med. Chem. 2001, 44, 863.
60. (b) Whipple, W. L.; Reich, H. J. J. Org. Chem. 1991, 56, 2911.