Rhodium(III)-catalyzed synthesis of pyridines from α,β- unsaturated ketoximes and internal alkynes

Synlett

Volumn , Issue 19, 2011, Pages 2789-2794

  Too, Pei Chui ^a   Noji, Toshiharu ^b   Lim, Ying Jie ^a   Li, Xingwei ^c   Chiba, Shunsuke ^a  

^a Nanyang Technological University   (Singapore)

^b TOHOKU UNIVERSITY   (Japan)

^c DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

alkynes; C H activation; oximes; pyridines; rhodium

Indexed keywords

2 NAPHTHYLPYRIDINE; 4 PHENYLBUT 3 ENE 2 ONE OXIME DERIVATIVE; ACETYLENE DERIVATIVE; ALKYNE; ALPHA BETA UNSATURATED KETOXIME DERIVATIVE; CARBON; DIALKYL ACETYLENE DERIVATIVE; DIARYL ACETYLENE DERIVATIVE; DIPHENYLACETYLENE; NITROGEN; OXIME ACETATE; OXIME DERIVATIVE; PYRIDINE; PYRIDINE DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; HYDROGEN BOND; PROCESS DEVELOPMENT; REACTION OPTIMIZATION; SYNTHESIS;

EID: 81855161545     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1289556     Document Type: Article

References (85)

1. Progress in Heterocyclic Chemistry Vol. 20 Gribble G W. Joule J A. Elsevier Oxford 2008 and other volumes in this series
2. Comprehensi v e Heterocyclic Chemistry III Katritzky A R. Ramsden C A. Scriven E F. V. Taylor R J. K. Pergamon Oxford 2008
3. Comprehensi v e Heterocyclic Chemistry II Katritzky A R. Rees C A. Scriven E F. V. Taylor R J. K. Pergamon Oxford 2008
4. Comprehensi v e Heterocyclic Chemistry II Katritzky A R. Rees C W. Scriven E F. V. McKillop A Pergamon Oxford 1996 and references therein
5. Eicher T, Hauptmann S, The Chemistry of Heterocycles Wiley-VCH Weinheim 2003
6. For recent reviews on synthesis of pyridines, see:, Hill M D., Chem. Eur. J. 2010 16 12052
7. Bagley M C., Glover C, Merritt E A., Synlett 2007 2459
8. Heller B, Hapke M, Chem. Soc. Rev. 2007 36 1085
9. Ciufolini M A., Chan B K., Heterocycles 2007 74 101
10. Henry G D., Tetrahedron 2004 60 6043
11. Varela J A., Saa C, Chem. Rev. 2003 103 3787
12. For recent selected reports on synthesis of pyridines, see:, Wang Y F., Toh K K., Ng P J. E., Chiba S, J. Am. Chem. Soc. 2011 133 6411
13. Nakamura I, Zhang D, Terada M, J. Am. Chem. Soc. 2010 132 7884
14. Chiba S, Xu Y.-J, Wang Y.-F, J. Am. Chem. Soc. 2009 131 12886
15. Wang Y F., Chiba S, J. Am. Chem. Soc. 2009 131 12570
16. Manning J R., Davies H M. L., J. Am. Chem. Soc. 2008 130 8602
17. Manning J R., Davies H M. L., J. Am. Chem. Soc. 2008 130 8602
18. Liu S, Liebeskind L S., J. Am. Chem. Soc. 2008 130 6918
19. Barluenga J, Fernández-Rodríguez M A., García- García P, Aguilar E, J. Am. Chem. Soc. 2008 130 2764
20. Parthasarathy K, Jeganmohan M, Cheng C.-H, Org. Lett. 2008 10 325
21. Movassaghi M, Hill M D., Ahmad O K., J. Am. Chem. Soc. 2007 129 10096
22. Dash J, Lechel T, Reissig H.-U, Org. Lett. 2007 9 5541
23. Trost B M., Gutierrez A C., Org. Lett. 2007 9 1473
24. Yamamoto Y, Kinpara K, Ogawa R, Nishiyama H, Itoh K, Chem. Eur. J. 2006 12 5618
25. Movassaghi M, Hill M D., J. Am. Chem. Soc. 2006 128 4592
26. Tanaka R, Yuza A, Watai Y, Suzuki D, Takayama Y, Sato F, Urabe H, J. Am. Chem. Soc. 2005 127 7774
27. McCormick M M., Duong H A., Zuo G, Louie J, J. Am. Chem. Soc. 2005 127 5030
28. For recent reviews, see:, Wencel-Delord J, Dröge T, Liu F, Glorius F, Chem. Soc. Rev. 2011 40 4740
29. Ackermann L, Chem. Rev. 2011 111 1315
30. Satoh T, Miura M, Chem. Eur. J. 2010 16 11212
31. Colby D A., Bergman R G., Ellman J A., Chem. Rev. 2010 110 624
32. Lyons T W., Sanford M S., Chem. Rev. 2010 110 1147
33. Sun C.-L, Li B.-J, Shi Z.-J, Chem. Commun. 2010 46 677
34. Ackermann L, Vicente R, Kapdi A R., Angew. Chem. Int. Ed. 2009 48 9792
35. Chen X, Engle K M., Wang D.-H, Yu J.-Q, Angew. Chem. Int. Ed. 2009 48 5094
36. Kulkarni A A., Daugulis O, Synthesis 2009 4087
37. Kakiuchi F, Kochi T, Synthesis 2008 3013
38. Park Y J., Park J.-W, Jun C.-H, Acc. Chem. Res. 2008 41 222
39. Kakiuchi F, Chatani N, Adv. Synth. Catal. 2003 345 1077
40. Ritleng V, Sirlin C, Pfeffer M, Chem. Rev. 2002 102 1731
41. Kakiuchi F, Murai S, Acc. Chem. Res. 2002 35 826
42. Dyker G, Angew. Chem. Int. Ed. 1999 38 1698
43. For selected reports on the ortho -metallation and carbon-carbon bond-formation sequence of aldimine and ketimine derivatives, see:, Gao K, Lee P.-S, Fujita T, Yoshikai N, J. Am. Chem. Soc. 2010 132 12249
44. Yoshikai N, Matsumoto A, Norinder J, Nakamura E, Angew. Chem. Int. Ed. 2009 48 2925
45. Kuninobu Y, Nishina Y, Matsuki T, Takai K, J. Am. Chem. Soc. 2008 130 14062
46. Kuninobu Y, Kikuchi K, Tokunaga Y, Nishina Y, Takai K, Tetrahedron 2008 64 5974
47. Kuninobu Y, Nishina Y, Nakagawa C, Takai K, J. Am. Chem. Soc. 2006 128 12376
48. Kuninobu Y, Tokunaga Y, Kawata A, Takai K, J. Am. Chem. Soc. 2006 128 202
49. Kuninobu Y, Kawata A, Takai K, J. Am. Chem. Soc. 2005 127 13498
50. Thalji R K., Ahrendt K A., Bergman R G., Ellman J A., J. Org. Chem. 2005 70 6775
51. Ueura K, Satoh T, Miura M, Org. Lett. 2005 7 2229
52. Lim S.-G, Ahn J.-A, Jun C.-H, Org. Lett. 2004 6 4687
53. Thalji R K., Ahrendt K A., Bergman R G., Ellman J A., J. Am. Chem. Soc. 2001 123 9692
54. Jun C.-H, Hong J.-B, Kim Y.-H, Chung K.-Y, Angew. Chem. Int. Ed. 2000 39 3440
55. Kakiuchi F, Sato T, Tsujimoto T, Yamauchi M, Chatani N, Murai S, Chem. Lett. 1998 1053
56. Fukuyama T, Chatani N, Kakiuchi F, Murai S, J. Org. Chem. 1997 62 5647
57. Kakiuchi F, Yamauchi M, Chatani N, Murai S, Chem. Lett. 1996 111
58. For a review, see:, Patureau F W., Glorius F, Angew. Chem. Int. Ed. 2011 50 1977
59. For a report on rhodium(III)-catalyzed redox-neutral synthesis of azaheterocycles from benzhydroxamic acid derivatives and oxime derivatives with alkynes, see:, Guimond N, Gorelsky S I., Fagnou K, J. Am. Chem. Soc. 2011 133 6449
60. Rakshit S, Grohmann C, Besset T, Glorius F, J. Am. Chem. Soc. 2011 133 2350
61. Too P C., Chua S H., Wong S H., Chiba S, J. Org. Chem. 2011 76 6159
62. Hyster T K., Rovis T, Chem. Sci. 2011 2 1606
63. Zhang X, Chen D, Zhao M, Zhao J, Jia A, Li X, Adv. Synth. Catal. 2011 353 719
64. Too P C., Wang Y.-F, Chiba S, Org. Lett. 2010 12 5688
65. Guimond N, Gouliaras C, Fagnou K, J. Am. Chem. Soc. 2010 132 6908
66. Although E / Z isomerization of the N-O bond of oxime 1k might be possible in the present reaction conditions, we are not certain whether the Z -isomer of 1k was converted into pyridine via its isomerization to E -isomer during this reaction. For isomerization of the oxime N-O bonds, see:, Johnson J E., Silk N M., Nalley E A., Arfan M, J. Org. Chem. 1981 46 546
67. Davies D L., Al-Duaij O, Fawcett J, Giardiello M, Hilton S T., Russell D R., Dalton Trans. 2003 4132
68. Li L, Brennessel W W., Jones W D., Organometallics 2009 28 3492
69. Han Y.-F, Li H, Hu P, Jin G.-X, Organometallics 2011 30 905
70. For selected reports on rhodium(III)-catalyzed oxidative C-H bond functionalization-C-N bond formation with alkynes, see:, Stuart D R., Alsabeh P, Kuhn M, Fagnou K, J. Am. Chem. Soc. 2010 132 18326
71. Chen J, Song G, Pan C.-L, Li X, Org. Lett. 2010 12 5426
72. Su Y, Zhao M, Han K, Song G, Li X, Org. Lett. 2010 12 5462
73. Hyster T K., Rovis T, J. Am. Chem. Soc. 2010 132 10565
74. Rakshit S, Patureau F W., Glorius F, J. Am. Chem. Soc. 2010 132 9585
75. Morimoto K, Hirano K, Satoh T, Miura M, Org. Lett. 2010 12 2068
76. Mochida S, Umeda N, Hirano K, Satoh T, Miura M, Chem. Lett. 2010 39 744
77. Guimond N, Fagnou K, J. Am. Chem. Soc. 2009 131 12050
78. Fukutani T, Umeda N, Hirano K, Satoh T, Miura M, Chem. Commun. 2009 5141
79. Stuart D R., Bertrand-Laperle M, Burgess K M. N., Fagnou K, J. Am. Chem. Soc. 2008 130 16474
80. For synthesis of pyridine derivatives by utilization of 6-electrocyclization of azatrienes generated by ortho -vinylation, see:, Parthasarathy K, Cheng C.-H, J. Org. Chem. 2009 74 9359
81. Colby D A., Bergman R G., Ellman J A., J. Am. Chem. Soc. 2008 130 3645
82. Yotphan S, Bergman R G., Ellman J A., J. Am. Chem. Soc. 2008 130 2452
83. Parthasarathy K, Jeganmohan M, Cheng C.-H, Org. Lett. 2008 10 325
84. Lim S.-G, Lee J H., Moon C W., Hong J.-B, Jun C.-H, Org. Lett. 2003 5 2759
85. Umeda N, Tsurugi H, Satoh T, Miura M, Angew. Chem. Int. Ed. 2008 47 4019