Nickel-catalyzed direct alkylation of heterocycles with α-bromo carbonyl compounds: C3-selective functionalization of 2-pyridones

Chemistry - A European Journal

Volumn 19, Issue 24, 2013, Pages 7691-7695

  Nakatani, Akihiro ^a   Hirano, Koji ^a   Satoh, Tetsuya ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

alkylation; homolytic radical aromatic substitution; nickel; pyridones; synthetic methods

Indexed keywords

1 ,5-CYCLOOCTADIENE; AROMATIC SUBSTITUTIONS; CATALYST SYSTEM; DIRECT ALKYLATION; FUNCTIONALIZATIONS; PYRIDONES; SELECTIVE FUNCTIONALIZATION; SYNTHETIC METHODS;

ALKYLATION; AROMATIC COMPOUNDS; CARBONYL COMPOUNDS;

NICKEL;

1,3 BIS(DIPHENYLPHOSPHINO)PROPANE; 1,3-BIS(DIPHENYLPHOSPHINO)PROPANE; 2 HYDROXYPYRIDINE; 2-HYDROXYPYRIDINE; BROMINATED HYDROCARBON; DRUG DERIVATIVE; NICKEL; PHOSPHINE DERIVATIVE; PROPANE; PYRIDONE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY;

ALKYLATION; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROCARBONS, BROMINATED; MOLECULAR STRUCTURE; NICKEL; PHOSPHINES; PROPANE; PYRIDONES;

EID: 84878558688     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301350     Document Type: Article

References (77)

1. M. Torres, S. Gil, M. Parra, Curr. Org. Chem. 2005, 9, 1757
2. I. M. Lagoja, Chem. Biodiversity 2005, 2, 1.
3. F. Christ, A. Voet, A. Marchand, S. Nicolet, B. A. Desimmie, D. Marchand, D. Bardiot, N. J. V. der Veken, B. V. Remoortel, S. V. Strelkov, M. D. Maeyer, P. Chaltin, Z. Debyser, Nat. Chem. Biol. 2010, 6, 442
4. G. Yu, P. N. P. Rao, M. A. Chowdhury, K. R. A. Abdellatif, Y. Dong, D. Das, C. A. Velázquez, M. R. Suresh, E. E. Knaus, Bioorg. Med. Chem. Lett. 2010, 20, 2168.
5. C. C. C. Johansson, T. J. Colacot, Angew. Chem. 2010, 122, 686
6. Angew. Chem. Int. Ed. 2010, 49, 676
7. F. Bellina, R. Rossi, Chem. Rev. 2010, 110, 1082; for early examples, see
8. T. Satoh, K. Kawamura, M. Miura, M. Nomura, Angew. Chem. 1997, 109, 1820
9. Angew. Chem. Int. Ed. Engl. 1997, 36, 1740
10. M. Palucki, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 11108
11. B. C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1997, 119, 12382
12. T. Satoh, J. Inoh, Y. Kawamura, M. Miura, M. Nomura, Bull. Chem. Soc. Jpn. 1998, 71, 2239.
13. W. Su, S. Raders, J. G. Verkade, X. Liao, J. F. Hartwig, Angew. Chem. 2006, 118, 5984
14. Angew. Chem. Int. Ed. 2006, 45, 5852
15. S. F. Yip, H. Y. Cheung, Z. Zhou, F. Y. Kwong, Org. Lett. 2007, 9, 3469
16. Y. Guo, B. Twamley, J. M. Shreeve, Chem. Commun. 2007, 3583
17. T. Hama, J. F. Hartwig, Org. Lett. 2008, 10, 1545; also see
18. J. M. Richter, B. W. Whitefield, T. J. Maimone, D. W. Lin, M. P. Castroviejo, P. S. Baran, J. Am. Chem. Soc. 2007, 129, 12857.
19. A. Studer, in Radicals in Organic Synthesis, Vol. 2, 1 st ed., (Eds.: P. Renaud, M. Sibi,), Wiley-VCH, Weinheim, 2001, p. 44
20. S. E. Vaillard, B. Schulte, A. Studer, in Modern Arylation Methods (Ed.:, L. Ackermann,), Wiley-VCH, Weinheim, 2009, p. 475
21. A. Studer, D. P. Curran, Angew. Chem. 2011, 123, 5122
22. Angew. Chem. Int. Ed. 2011, 50, 5018; for selected recent advances, see
23. S. Yanagisawa, K. Ueda, T. Taniguchi, K. Itami, Org. Lett. 2008, 10, 4673
24. E. Shirakawa, K.-i. Itoh, T. Higashino, T. Hayashi, J. Am. Chem. Soc. 2010, 132, 15537
25. W. Liu, H. Cao, H. Zhang, K. H. Chung, C. He, H. Wang, F. Y. Kwong, A. Lei, J. Am. Chem. Soc. 2010, 132, 16737
26. C.-L. Sun, H. Li, D.-G. Yu, M. Yu, X. Zhou, X.-Y. Lu, K. Huang, S.-F. Zheng, B.-J. Li, Z.-J. Shi, Nat. Chem. 2010, 2, 1044
27. I. B. Seiple, S. Su, R. A. Rodriguez, R. Gianatassio, Y. Fujiwara, A. L. Sobel, P. S. Baran, J. Am. Chem. Soc. 2010, 132, 13194
28. D. A. Nagib, D. W. C. MacMillan, Nature 2011, 480, 224
29. Y. Fujiwara, J. A. Dixon, R. A. Rodriguez, R. D. Baxter, D. D. Dixon, M. R. Collins, D. G. Blackmond, P. S. Baran, J. Am. Chem. Soc. 2012, 134, 1494
30. Y. Fujiwara, J. A. Dixon, F. O'Hara, E. D. Funder, D. D. Dixon, R. A. Rodriguez, R. D. Baxter, B. Herlé, N. Sach, M. R. Collins, Y. Ishihara, P. S. Baran, Nature 2012, 492, 95.
31. L. Furst, B. S. Matsuura, J. M. R. Narayanam, J. W. Tucker, C. R. J. Stephenson, Org. Lett. 2010, 12, 3104
32. C.-J. Wallentin, J. D. Nguyen, P. Finkbeiner, C. R. J. Stephenson, J. Am. Chem. Soc. 2012, 134, 8875
33. H. Jiang, C. Huang, J. Guo, C. Zeng, Y. Zhang, S. Yu, Chem. Eur. J. 2012, 18, 15158.
34. III salts, see:, E. Baciocchi, E. Muraglia, J. Org. Chem. 1993, 58, 7610.
35. Y. M. Osornio, R. Cruz-Almanza, V. Jiménez-Montaño, L. D. Miranda, Chem. Commun. 2003, 2316
36. O. Guadarrama-Morales, F. Méndez, L. D. Miranda, Tetrahedron Lett. 2007, 48, 4515; for the alkylation with highly reactive α-iodoesters under photolytic conditions, see
37. J. H. Byers, A. DeWitt, C. G. Nasveschuk, J. E. Swigor, Tetrahedron Lett. 2004, 45, 6587.
38. D. Dube, L. Dube, M. Gallant, P. Lacombe, D. Deschenes, D. MacDonald, PCT. Int. Appl. 2004, WO 2004096220, A1 2004965063 (CAN 141:410960); for the trifluoromethylation of 2-hydroxypyridine (a tautomer of NH-2-pyridone), see
39. T. Kino, Y. Nagase, Y. Ohtsuka, K. Yamamoto, D. Uraguchi, K. Tokuhisa, T. Yamakawa, J. Fluorine Chem. 2010, 131, 98; very recently, Hong et al. reported a palladium-catalyzed C3-selective direct alkenylation of 2-quinolinones, see
40. M. Min, Y. Kim, S. Hong, Chem. Commun. 2013, 49, 196.
41. T. Itahara, F. Ouseto, Synthesis 1984, 488
42. K. Hirota, Y. Isobe, Y. Kitade, Y. Maki, Synthesis 1987, 495
43. H. B. Ge, M. J. Niphakis, G. I. Georg, J. Am. Chem. Soc. 2008, 130, 3708
44. Y. Chen, F. Wang, A. Jia, X. Li, Chem. Sci. 2012, 3, 3231; C5-selective chlorination with N-chlorosuccinimide has also been reported, see
45. L. A. Paquette, W. C. Farley, J. Org. Chem. 1967, 32, 2725.
46. Y. Nakao, H. Idei, K. S. Kanyiva, T. Hiyama, J. Am. Chem. Soc. 2009, 131, 15996
47. R. Tamura, Y. Yamada, Y. Nakao, T. Hiyama, Angew. Chem. 2012, 124, 5777
48. Angew. Chem. Int. Ed. 2012, 51, 5679.
49. Attempts to apply the simple N-methylindole were unsuccessful due to competitive formation of the diindolylmethane, see:, P. K. Pradhan, S. Dey, V. S. Giri, P. Jaisankar, Synthesis 2005, 1779.
50. For functionalized azulenes in material chemistry, see:, S.-i. Takemura, M. Yamamoto, A. Nakagawa, T. Iwata, T. Minematsu, H. Takemura, Tetrahedron 2012, 68, 8318, and references therein. The alkylated products were isolated as the corresponding methyl esters after purification processes. See the Supporting Information for the detailed procedure.
51. J. S. Zhou, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 14726
52. J. S. Zhou, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 1340
53. D. A. Powell, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 7788
54. D. A. Powell, T. Maki, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 510
55. F. González-Bobes, G. C. Fu, J. Am. Chem. Soc. 2006, 128, 5360
56. B. Saito, G. C. Fu, J. Am. Chem. Soc. 2007, 129, 9602
57. N. A. Strotman, S. Sommer, G. C. Fu, Angew. Chem. 2007, 119, 3626
58. Angew. Chem. Int. Ed. 2007, 46, 3556; for examples of asymmetric variants, see
59. S. Son, G. C. Fu, J. Am. Chem. Soc. 2008, 130, 2756
60. X. Dai, N. A. Stortman, G. C. Fu, J. Am. Chem. Soc. 2008, 130, 3302
61. B. Saito, G. C. Fu, J. Am. Chem. Soc. 2008, 130, 6694
62. S. Lou, G. C. Fu, J. Am. Chem. Soc. 2010, 132, 1264
63. S. Lou, G. C. Fu, J. Am. Chem. Soc. 2010, 132, 5010
64. P. M. Lundin, G. C. Fu, J. Am. Chem. Soc. 2010, 132, 11027
65. J. Choi, G. C. Fu, J. Am. Chem. Soc. 2012, 134, 9102.
66. C. Liu, S. Tang, D. Liu, J. Yuan, L. Zheng, L. Meng, A. Lei, Angew. Chem. 2012, 124, 3698
67. Angew. Chem. Int. Ed. 2012, 51, 3638.
68. T. J. Anderson, G. D. Jones, D. A. Vicic, J. Am. Chem. Soc. 2004, 126, 8100.
69. K. Wakabayashi, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2001, 123, 5374
70. H. Ohmiya, T. Tsuji, H. Yorimitsu, K. Oshima, Chem. Eur. J. 2004, 10, 5640
71. W. Affo, H. Ohmiya, T. Fujioka, Y. Ikeda, T. Nakamura, H. Yorimitsu, K. Oshima, Y. Imamura, T. Mizuta, K. Miyoshi, J. Am. Chem. Soc. 2006, 128, 8068
72. K. S. Bloome, E. J. Alexanian, J. Am. Chem. Soc. 2010, 132, 12823
73. K. S. Bloome, R. L. McMahen, E. J. Alexanian, J. Am. Chem. Soc. 2011, 133, 20146
74. M. E. Weiss, L. M. Kreis, A. Lauber, E. M. Carreira, Angew. Chem. 2011, 123, 11321
75. Angew. Chem. Int. Ed. 2011, 50, 11125.
76. I species 9 followed by β-H elimination can be an alternative, but this type of reduction process on the nickel center can be less favorable, which is supported by DFT calculations; see:, B.-L. Lin, L. Liu, Y. Fu, S.-W. Luo, Q. Chen, Q.-X. Guo, Organometallics 2004, 23, 2114, and Ref. [16].
77. D. R. Artis, I.-S. Cho, S. Jaime-Figueroa, J. M. Muchowski, J. Org. Chem. 1994, 59, 2456.