Ruthenium-catalyzed transfer-hydrogenative cyclization of 1,6-diynes with hantzsch 1,4-dihydropyridine as a H2 surrogate

Chemistry - A European Journal

Volumn 19, Issue 36, 2013, Pages 12034-12041

  Yamamoto, Yoshihiko ^a   Mori, Shota ^a   Shibuya, Masatoshi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

alkenes; alkynes; cyclization; ruthenium; transfer hydrogenation

Indexed keywords

ALKYNES; CYCLOALKENES; EXOCYCLIC 1 ,3-DIENES; HANTZSCH 1 ,4-DIHYDROPYRIDINE; REACTION CONDITIONS; RUTHENIUM CATALYSTS; SUBSTRATE STRUCTURE; TRANSFER HYDROGENATIONS;

HYDROCARBONS; HYDROGENATION; OLEFINS; PYRIDINE; RUTHENIUM;

CYCLIZATION;

EID: 84883231463     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301846     Document Type: Article

References (87)

1. Á. Molnár, A. Sárkány, M. Varga, J. Mol. Catl. A: Chem. 2001, 173, 185-221
2. S. Bailey, F. King, Catalytic hydrogenation and Dehydrogenation in Fine Chemicals through Heterogeneous Catalysis (Eds.:, R. A. Sheldon, H. van Bekkum,), Wiley-VCH, Weinheim, 2001, Chapter 8, pp. 351-471
3. M. Crespo-Quesada, F. Cárdenas-Lizana, A.-L. Dessimoz, L. Kiwi-Minsker, ACS Catal. 2012, 2, 1773-1786.
4. H. Lindlar, Helv. Chim. Acta 1952, 35, 446-450
5. H. Lindlar, R. Dubuis, Org. Synth. 1966, 46, 89-91
6. J. G. Ulan, W. F. Maier, D. A. Smith, J. Org. Chem. 1987, 52, 3132-3142
7. M. García-Mota, J. Gõmez-Días, G. Novell-Leruth, C. Vargas-Fuentes, L. Bellarosa, B. Bridier, J. Pérez-Ramírez, N. Lõpez, Theor. Chem. Acc. 2011, 128, 663-673, and the references therein.
8. A. M. Kluwer, C. J. Elsevier, Homogeneous Hydrogenation of Alkynes and Dienes in Handbook of Homogeneous Hydrogenation, Vol. 1 (Eds.:, J. G. de Vries, C. J. Elsevier,), Wiley-VCH, Weinheim, 2007, Chapter 14, pp. 371-412.
9. B. M. Trost, R. Braslau, Tetrahedron Lett. 1989, 30, 4657-4660
10. L.-L. Wei, L.-M. Wei, W.-B. Pan, S.-P. Leou, M. J. Wu, Tetrahedron Lett. 2003, 44, 1979-1981
11. V. Jurčík, S. P. Nolan, C. S. J. Cazin, Chem. Eur. J. 2009, 15, 2509-2511
12. J. Li, R. Hua, T. Liu, J. Org. Chem. 2010, 75, 2966-2970
13. J. Broggi, V. Jurčík, O. Songis, A. Poater, L. Cavallo, A. M. Z. Slawin, C. S. J. Cazin, J. Am. Chem. Soc. 2013, 135, 4588-4591.
14. M. W. van Laren, C. J. Elsevier, Angew. Chem. 1999, 111, 3926-3929
15. Angew. Chem. Int. Ed. 1999, 38, 3715-3717
16. M. W. van Laren, M. A. Duin, C. Klerk, M. Naglia, D. Rogolino, P. Pelagatti, A. Bacchi, C. Pelizzi, C. J. Elsevier, Organometallics 2002, 21, 1546-1553
17. J. W. Sprengers, J. Wassenaar, N. D. Clement, K. J. Cavell, C. J. Elsevier, Angew. Chem. 2005, 117, 2062-2065
18. Angew. Chem. Int. Ed. 2005, 44, 2026-2029
19. A. M. Kluwer, T. S. Koblenz, T. Jonischkeit, K. Woelk, C. J. Elsevier, J. Am. Chem. Soc. 2005, 127, 15470-15480
20. P. Hauwert, G. Maestri, J. W. Sprengers, M. Catellani, C. J. Elsevier, Angew. Chem. 2008, 120, 3267-3270
21. Angew. Chem. Int. Ed. 2008, 47, 3223-3226
22. P. Hauwert, R. Boerleider, S. Warsink, J. J. Weigand, C. J. Elsevier, J. Am. Chem. Soc. 2010, 132, 16900-16910
23. P. Hauwert, J. J. Dunsford, D. S. Tromp, J. J. Weigand, M. Lutz, K. J. Cavell, C. J. Elsevier, Organometallics 2013, 32, 131-140.
24. E. Shirakawa, H. Otsuka, T. Hayashi, Chem. Commun. 2005, 5885-5886
25. F. Luo, C. Pan, W. Wang, Z. Ye, J. Cheng, Tetrahedron 2010, 66, 1399-1403
26. R. Shen, T. Chen, Y. Zhao, R. Qiu, Y. Zhou, S. Yin, X. Wang, M. Goto, L.-B. Han, J. Am. Chem. Soc. 2011, 133, 17037-17044.
27. R. R. Schrock, J. A. Osborn, J. Am. Chem. Soc. 1976, 98, 2143-2147; Cr
28. M. Sodeoka, M. Shibasaki, J. Org. Chem. 1985, 50, 1147-1149; Ir
29. K. Tani, A. Iseki, T. Yamagata, Chem. Commun. 1999, 1821-1822; Ni
30. R. Barrios-Francisco, J. J. García, Inorg. Chem. 2009, 48, 386-393
31. A. Reyes-Sánchez, F. Cañavera-Buelvas, R. Barrios-Francisco, O. L. Cifuentes-Vaca, M. Flores-Alamo, J. J. García, Organometallics 2011, 30, 3340-3345; Fe
32. S. Enthaler, M. Haberger, E. Irran, Chem. Asian J. 2011, 6, 1613-1623; V
33. H. S. La Pierre, J. Arnold, F. D. Toste, Angew. Chem. 2011, 123, 3986-3989
34. Angew. Chem. Int. Ed. 2011, 50, 3900-3903; Nb
35. T. L. Gianetti, N. C. Tomson, J. Arbold, R. G. Bergman, J. Am. Chem. Soc. 2011, 133, 14904-14907; Cu
36. K. Semba, T. Fujihara, T. Xu, J. Terao, Y. Tsuji, Adv. Synth. Catal. 2012, 354, 1542-1550
37. A. M. Whittaker, G. Lalic, Org. Lett. 2013, 15, 1112-1115.
38. Y. Shvo, I. Goldberg, D. Czerkie, D. Reshef, Z. Stein, Organometallics 1997, 16, 133-138
39. D. Schleyer, H. G. Niessen, J. Bargon, New J. Chem. 2001, 25, 423-426
40. Y. Gao, M. C. Jennings, R. J. Puddephatt, Can. J. Chem. 2001, 79, 915-921
41. H. H. Horváth, F. Joõ, React. Kinet. Catal. Lett. 2005, 85, 355-360
42. J.-P. Djukic, K. Parkhomenko, A. Hijazi, A. Chemmi, L. Allouche, L. Brelot, M. Pfeffer, L. Ricard, X.-F. Le Goff, Dalton Trans. 2009, 2695-2711
43. C. Belber, N. M. Neisius, B. Plietker, Chem. Eur. J. 2010, 16, 12214-12220
44. J. Li, R. Hua, Chem. Eur. J. 2011, 17, 8462-8465
45. K. Radkowski, B. Sundararaju, A. Fürstner, Angew. Chem. 2013, 125, 373-378
46. Angew. Chem. Int. Ed. 2013, 52, 355-360.
47. J. Lõpez-Serrano, S. B. Duckett, S. Aiken, K. Q. A. Leñero, E. Drent, J. P. Dunne, D. Konya, A. C. Whitwood, J. Am. Chem. Soc. 2007, 129, 6513-6527
48. J. Lõpez-Serrano, A. Lledõs, S. B. Duckett, Organometallics 2008, 27, 43-52
49. M. Boutain, S. B. Duckett, J. P. Dunne, C. Godard, J. M. Hernández, A. J. Holmes, I. G. Khazal, J. Lõpez-Serrano, Dalton Trans. 2010, 39, 3495-3500.
50. B. M. Trost, F. Rise, J. Am. Chem. Soc. 1987, 109, 3161-3163
51. B. M. Trost, D. C. Lee, J. Am. Chem. Soc. 1988, 110, 7255-7258
52. C. H. Oh, H. H. Jung, Tetrahedron Lett. 1999, 40, 1535-1538.
53. H.-Y. Jang, M. J. Krische, J. Am. Chem. Soc. 2004, 126, 7875-7800
54. H.-Y. Jang, F. W. Hughes, H. Gong, J. Zhang, J. S. Brodbelt, M. J. Krische, J. Am. Chem. Soc. 2005, 127, 6174-6175.
55. I. G. Jung, J. Seo, S. I. Lee, S. Y. Choi, Y. K. Chung, Organometallics 2006, 25, 4240-4242.
56. K. T. Sylvester, P. J. Chirik, J. Am. Chem. Soc. 2009, 131, 8772-8774
57. J. M. Hoyt, K. T. Sylvester, S. P. Semproni, P. J. Chirik, J. Am. Chem. Soc. 2013, 135, 4862-4877.
58. J. H. Park, S. M. Kim, Y. K. Chung, Chem. Eur. J. 2011, 17, 10852-10856.
59. K. Yamashita, Y. Nagashima, Y. Yamamoto, H. Nishiyama, Chem. Commun. 2011, 47, 11552-11554.
60. 2 surrogate has been reported; see:, R. L. Patman, M. R. Chaulagain, V. M. Williams, M. J. Krische, J. Am. Chem. Soc. 2009, 131, 2066-2067.
61. Y. Yamamoto, K. Yamashita, H. Nishiyama, Chem. Commun. 2011, 47, 1556-1558
62. K. Yamashita, Y. Yamamoto, H. Nishiyama, J. Am. Chem. Soc. 2012, 134, 7660-7663
63. Y. Yamamoto, K. Fukatsu, H. Nishiyama, Chem. Commun. 2012, 48, 7985-7987.
64. B. M. Trost, M. T. Rudd, J. Am. Chem. Soc. 2003, 125, 11516-11517.
65. A. Hantzsch, Justus Liebigs Ann. Chem. 1882, 215, 1-82; for reviews of the chemistry of dihydropyridines, see
66. U. Eisner, J. Kuthan, Chem. Rev. 1972, 72, 1-42
67. D. M. Stout, A. I. Meyers, Chem. Rev. 1982, 82, 223-243
68. R. Lavilla, J. Chem. Soc. Perkin Trans. 1 2002, 1141-1156.
69. S.-L. You, Chem. Asian J. 2007, 2, 820-827
70. S. G. Ouellet, A. M. Walji, D. W. C. MacMillan, Acc. Chem. Res. 2007, 40, 1327-1339
71. M. Rueping, E. Sugiono, F. R. Schoepke, Synlett 2010, 852-865.
72. X.-X. Shen, Q. Liu, R.-G. Xing, B. Zhou, Catal. Lett. 2008, 126, 361-366
73. Q. Liu, J. Li, X.-X. Shen, R.-G. Xing, J. Yang, Z. Liu, B. Zhou, Tetrahedron Lett. 2009, 50, 1026-1028
74. Q.-y. Meng, Q. Liu, J. Li, R.-G. Xing, X.-X. Shen, B. Zhou, Synlett 2009, 3283-3286
75. Y. Zhao, Q. Liu, J. Li, Z. Liu, B. Zhou, Synlett 2010, 1870-1872
76. R.-G. Xing, Y.-N. Li, Q. Liu, Q.-Y. Meng, J. Li, X.-X. Shen, Z. Liu, B. Zhou, X. Yao, Z.-L. Liu, Eur. J. Org. Chem. 2010, 6627-6632
77. R.-G. Xing, Y.-N. Li, Q. Liu, Y.-F. Han, X. Wei, J. Li, B. Zhou, Synthesis 2011, 2066-2072.
78. M. Zhang, H. Yang, Y. Zhang, C. Zhu, W. Li, Y. Cheng, H. Hu, Chem. Commun. 2011, 47, 6605-6607
79. X.-Y. Liu, C.-M. Che, Org. Lett. 2009, 11, 4204-4207
80. X.-Y. Liu, Z. Guo, S. S. Dong, X.-H. Li, C.-M. Che, Chem. Eur. J. 2011, 17, 12932-12945
81. Z.-Y. Han, H. Xia, X.-H. Chen, L.-Z. Gong, J. Am. Chem. Soc. 2009, 131, 9182-9183
82. X.-F. Tu, L.-Z. Gong, Angew. Chem. 2012, 124, 11508-11511
83. Angew. Chem. Int. Ed. 2012, 51, 11346-11349.
84. S. Steines, U. Englert, B. Drießen-Hölscher, Chem. Commun. 2000, 217-218
85. H. G. Niessen, D. Schleyer, S. Wiemann, J. Bargon, S. Steines, Driessen-Hoelscher, Magn. Reson. Chem. 2000, 38, 747-750.
86. Y. Yamamoto, T. Arakawa, R. Ogawa, K. Itoh, J. Am. Chem. Soc. 2003, 125, 12143-12160.
87. Y. Yamamoto, A. Nagata, H. Nagata, Y. Ando, Y. Arikawa, K. Tatsumi, K. Itoh, Chem. Eur. J. 2003, 9, 2469-2483.