Convenient synthesis of quinolines from α-2-nitroaryl alcohols and alcohols via a ruthenium-catalyzed hydrogen transfer strategy

ChemCatChem

Volumn 7, Issue 2, 2015, Pages 349-353

  Xie, Feng ^a,b   Zhang, Min ^a   Chen, Mengmeng ^b   Lv, Wan ^a   Jiang, Huanfeng ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b JIANGNAN UNIVERSITY   (China)

Author keywords

Alcohols; Annulation; Homogeneous catalysis; Hydrogen transfer; Quinolines; Ruthenium

Indexed keywords

ALCOHOLS; CATALYSIS; HYDROGEN; REACTION KINETICS; REDUCING AGENTS; SYNTHESIS (CHEMICAL);

ANNULATION; HOMOGENEOUS CATALYSIS; HYDROGEN TRANSFER; QUINOLINE DERIVATIVE; QUINOLINES; RUTHENIUM CATALYSTS; STRAIGHT-FORWARD METHOD; SUBSTITUTED PRODUCTS;

RUTHENIUM;

EID: 84920857109     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201402832     Document Type: Article

References (97)

1. a) W. Zuo, A. J. Lough, Y. F. Li, R. H. Morris, Science 2013, 342, 1080-1083;
2. b) G. Wienhöfer, F. A. Westerhaus, K. Junge, M. Beller, J. Organomet. Chem. 2013, 744, 156-159;
3. c) S. Werkmeister, C. Bornschein, K. Junge, M. Beller, Chem. Eur. J. 2013, 19, 4437-4440;
4. d) R. V. Jagadeesh, G. Wienhoefer, F. A. Westerhaus, A.-E. Surkus, H. Junge, K. Junge, M. Beller, Chem. Eur. J. 2011, 17, 14375-14379;
5. e) S. Horn, M. Albrecht, Chem. Commun. 2011, 47, 8802-8804;
6. f) D. Gnanamgari, A. Moores, E. Rajaseelan, R. H. Crabtree, Organometallics 2007, 26, 1226-1230.
7. a) M. M. Chen, M. Zhang, B. Xiong, Z. D. Tan, W. Lv, H. F. Jiang. Org. Lett. 2014, 16, DOI: 10.1021/ol503052s;
8. b) X. T. Wang, M. M. Chen, F. Xie, M. Zhang, RSC Adv. 2014, 4, 14744-14751;
9. c) F. Xie, X. T. Wang, F. X. Yan, T. Wang, M. M. Chen, Y. Q. Ding, RSC Adv. 2013, 3, 6022;
10. d) F. Xie, M. M. Chen, X. T. Wang, H. Jiang, M. Zhang, Org. Biomol. Chem. 2014, 12, 2761-2768;
11. e) J. R. Khusnutdinova, Y. Ben-David, D. Milstein, J. Am. Chem. Soc. 2014, 136, 2998-3001;
12. f) T. Hille, T. Irrgang, R. Kempe, Chem. Eur. J. 2014, 20, 5569-5572;
13. g) S. Michlik, R. Kempe, Nat. Chem. 2013, 5, 140-144;
14. h) D. Srimani, Y. Ben-David, D. Milstein, Chem. Commun. 2013, 49, 6632-6634;
15. i) D. Srimani, Y. Ben-David, D. Milstein, Angew. Chem. Int. Ed. 2013, 52, 4012-4015;
16. Angew. Chem. 2013, 125, 4104-4107;
17. j) D. Srimani, E. Balaraman, P. Hu, Y. Ben-David, D. Milstein, Adv. Synth. Catal. 2013, 355, 2525-2530;
18. k) C. Gunanathan, D. Milstein, Science 2013, 341, 249;
19. l) E. Balaraman, E. Khaskin, G. Leitus, D. Milstein, Nat. Chem. 2013, 5, 122-125;
20. m) D. Srimani, E. Balaraman, B. Gnanaprakasam, Y. Ben-David, D. Milstein, Adv. Synth. Catal. 2012, 354, 2403-2406;
21. n) M. H. G. Prechtl, K. Wobser, N. Theyssen, Y. Ben-David, D. Milstein, W. Leitner, Catal. Sci. Technol. 2012, 2, 2039-2042;
22. o) E. Kossoy, Y. Diskin-Posner, G. Leitus, D. Milstein, Adv. Synth. Catal. 2012, 354, 497-504;
23. p) R. N. Monrad, R. Madsen, Org. Biomol. Chem. 2011, 9, 610-615;
24. q) B. Gnanaprakasam, J. Zhang, D. Milstein, Angew. Chem. Int. Ed. 2010, 49, 1468-1471;
25. Angew. Chem. 2010, 122, 1510-1513.
26. a) M. Chen, M. Zhang, F. Xie, X. Wang, H. Jiang, ChemCatChem 2014, 6, 2993-2997;
27. b) D. Wang, K. Zhao, X. Yu, H. Miao, Y. Ding, RSC Adv. 2014, 4, 42924-42929;
28. c) S. Michlik, T. Hille, R. Kempe, Adv. Synth. Catal. 2012, 354, 847-862;
29. d) M. Zhang, S. Imm, S. Baehn, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2011, 50, 11197-11201;
30. Angew. Chem. 2011, 123, 11393-11397;
31. e) S. Imm, S. Bähn, M. Zhang, L. Neubert, H. Neumann, F. Klasovsky, J. Pfeffer, T. Haas, M. Beller, Angew. Chem. Int. Ed. 2011, 50, 7599-7603;
32. Angew. Chem. 2011, 123, 7741-7745;
33. f) R. H. Crabtree, Organometallics 2011, 30, 17-19;
34. g) G. Guillena, D. J. Ramon, M. Yus, Chem. Rev. 2010, 110, 1611-1641;
35. h) G. E. Dobereiner, R. H. Crabtree, Chem. Rev. 2010, 110, 681-703;
36. i) T. D. Nixon, M. K. Whittlesey, J. M. J. Williams, Dalton Trans. 2009, 753-762;
37. j) M. H. S. A. Hamid, C. L. Allen, G. W. Lamb, A. C. Maxwell, H. C. Maytum, A. J. A. Watson, J. M. J. Williams, J. Am. Chem. Soc. 2009, 131, 1766-1774;
38. k) G. W. Lamb, J. M. J. Williams, Chim. Oggi 2008, 26, 17-19;
39. l) M. H. S. A. Hamid, P. A. Slatford, J. M. J. Williams, Adv. Synth. Catal. 2007, 349, 1555-1575;
40. m) G. Guillena, D. J. Ramon, M. Yus, Angew. Chem. Int. Ed. 2007, 46, 2358-2364;
41. Angew. Chem. 2007, 119, 2410-2416;
42. n) M. H. S. A. Hamid, J. M. J. Williams, Chem. Commun. 2007, 725-727.
43. a) F. Xie, M. Zhang, H. Jiang, M. Chen, W. Lv, A. Zheng, X. Jian, Green Chem. Green. Chem. 2014, 16, DOI: 10.1039/C4GC01316F;
44. b) M. Zhang, H. Neumann, M. Beller, Angew. Chem. Int. Ed. 2013, 52, 597-601;
45. Angew. Chem. 2013, 125, 625-629;
46. c) M. Zhang, X. Fang, H. Neumann, M. Beller, J. Am. Chem. Soc. 2013, 135, 11384-11388;
47. d) K. Yuan, F. Jiang, Z. Sahli, M. Achard, T. Roisnel, C. Bruneau, Angew. Chem. Int. Ed. 2012, 51, 8876-8880;
48. Angew. Chem. 2012, 124, 9006-9010;
49. e) X. Cui, C. Zhang, F. Shi, Y. Deng, Chem. Commun. 2012, 48, 9391-9393;
50. f) A. Zanardi, J. A. Mata, E. Peris, Chem. Eur. J. 2010, 16, 10502-10506;
51. g) S. Michlik, R. Kempe, Chem. Eur. J. 2010, 16, 13193-13198;
52. h) B. Blank, R. Kempe, J. Am. Chem. Soc. 2010, 132, 924-925;
53. i) B. Blank, S. Michlik, R. Kempe, Chem. Eur. J. 2009, 15, 3790-3799.
54. a) L. Tang, X. Guo, Y. Yang, Z. Zha, Z. Wang, Chem. Commun. 2014, 50, 6145-6148;
55. b) H. Wang, X. Cao, F. Xiao, S. Liu, G.-J. Deng, Org. Lett. 2013, 15, 4900-4903;
56. c) F. Xiao, Y. Liu, C. Tang, G.-J. Deng, Org. Lett. 2012, 14, 984-987;
57. d) M. Wu, X. Hu, J. Liu, Y. Liao, G.-J. Deng, Org. Lett. 2012, 14, 2722-2725;
58. e) Y. Liu, W. Chen, C. Feng, G. Deng, Chem. Asian J. 2011, 6, 1142-1146;
59. f) S. Liu, R. Chen, G.-J. Deng, Chem. Lett. 2011, 40, 489-491;
60. g) C. Feng, Y. Liu, S. Peng, Q. Shuai, G. Deng, C.-J. Li, Org. Lett. 2010, 12, 4888-4891.
61. a) N. Paul, S. Muthusubramanian, Med. Chem. Res. 2014, 23, 1612-1621;
62. b) D. D. N'Da, P. J. Smith, Med. Chem. Res. 2014, 23, 1214-1224;
63. c) S. Mukherjee, M. Pal, Curr. Med. Chem. 2013, 20, 4386-4410;
64. d) N. C. Vieira, C. Herrenknecht, J. Vacus, A. Fournet, C. Bories, B. Figadere, L. S. Espindola, P. M. Loiseau, Biomed. Pharmacother. 2008, 62, 684-689;
65. e) R. J. Altenbach, H. Liu, P. N. Banfor, K. E. Browman, G. B. Fox, R. M. Fryer, V. A. Komater, K. M. Krueger, K. Marsh, T. R. Miller, J. B. Pan, L. Pan, M. Sun, C. Thiffault, J. Wetter, C. Zhao, D. Zhou, T. A. Esbenshade, A. A. Hancock, M. D. Cowart, J. Med. Chem. 2007, 50, 5439-5448;
66. f) N. Muruganantham, R. Sivakumar, N. Anbalagan, V. Gunasekaran, J. T. Leonard, Biol. Pharm. Bull. 2004, 27, 1683-1687;
67. g) M. P. Maguire, K. R. Sheets, K. McVety, A. P. Spada, A. Zilberstein, J. Med. Chem. 1994, 37, 2129-2137.
68. a) X. Zuo, Z. Dong, W. Li, G. Yuan, Z. Cui, Y. Liu, X. Li, Mater. Technol. 2014, 48, 59-66;
69. b) S. Ou, Z. Lin, C. Duan, H. Zhang, Z. Bai, Chem. Commun. 2006, 4392-4394.
70. a) S. Zhu, W. Lin, L. Yuan, Dyes Pigm. 2013, 99, 465-471;
71. b) N. Shahabadi, M. Maghsudi, Dyes Pigm. 2013, 96, 377-382;
72. c) M. Hranjec, E. Horak, M. Tireli, G. Pavlovic, G. Karminski-Zamola, Dyes Pigm. 2012, 95, 644-656;
73. d) L. Montero de Espinosa, J. C. Ronda, M. Galia, V. Cadiz, J. Polym. Sci. Part A 2010, 48, 869-878;
74. e) D. G. Krotko, K. V. Fedotov, A. I. Tolmachev, Dyes Pigm. 2005, 65, 183-189.
75. a) P. Friedlaender, Ber. Dtsch. Chem. Ges. 1882, 15, 2572-2575;
76. b) Z. H. Skaup, Ber. Dtsch. Chem. Ges. 1880, 13, 2086-2087;
77. c) A. Combes, Bull. Soc. Chim. Fr. 1888, 49, 89.
78. a) P. Zhao, X. Yan, H. Yin, C. Xi, Org. Lett. 2014, 16, 1120-1123;
79. b) M. Chen, N. Sun, Y. Liu, Org. Lett. 2013, 15, 5574-5577;
80. c) X. Ji, H. Huang, Y. Li, H. Chen, H. Jiang, Angew. Chem. Int. Ed. 2012, 51, 7292-7296;
81. Angew. Chem. 2012, 124, 7404-7408;
82. d) X. Zhang, T. Yao, M. A. Campo, R. C. Larock, Tetrahedron 2010, 66, 1177-1187;
83. e) B. Gabriele, R. Mancuso, E. Lupinacci, R. Spina, G. Salerno, L. Veltri, A. Dibenedetto, Tetrahedron 2009, 65, 8507-8512.
84. A. A. Al-Qahtani, T. M. Al-Turki, M. Khan, A. A. Mousa, H. Z. Alkhathlan, Asian J. Chem. 2013, 25, 6055-6058.
85. a) H. Vander Mierde, P. Van Der Voot, D. De Vos, F. Verpoort, Eur. J. Org. Chem. 2008, 1625-1631;
86. b) R. Martínez, D. J. Ramon, M. Yus, J. Org. Chem. 2008, 73, 9778-9780;
87. c) H. Vander Mierde, N. Ledoux, B. Allaert, P. Van Der Voort, R. Drozdzak, D. De Vos, F. Verpoort, New J. Chem. 2007, 31, 1572-1574;
88. d) R. Martínez, D. J. Ramon, M. Yus, Tetrahedron 2006, 62, 8982-8987;
89. e) C. S. Cho, B. T. Kim, H.-J. Choi, T.-J. Kim, S. C. Shim, Tetrahedron 2003, 59, 7997-8002.
90. A.-H. Li, E. Ahmed, X. Chen, M. Cox, A. P. Crew, H.-Q. Dong, M. Jin, L. Ma, B. Panicker, K. W. Siu, A. G. Steinig, K. M. Stolz, P. A. R. Tavares, B. Volk, Q. Weng, D. Werner, M. J. Mulvihill, Org. Biomol. Chem. 2007, 5, 61-64.
91. a) P. B. Arockiam, C. Fischmeister, C. Bruneau, P. H. Dixneuf, Angew. Chem. Int. Ed. 2010, 49, 6629-6632;
92. Angew. Chem. 2010, 122, 6779-6782;
93. b) I. Özdemir, S. Demir, B. Cetinkaya, C. Gourlaouen, F. Maseras, C. Bruneau, P. H. Dixneuf, J. Am. Chem. Soc. 2008, 130, 1156-1157.
94. a) B. Peña, A. David, C. Pavani, M. S. Baptista, J.-P. Pellois, C. Turro, K. R. Dunbar, Organometallics 2014, 33, 1100-1103;
95. b) J. H. Barnard, C. Wang, N. G. Berry, J. Xiao, Chem. Sci. 2013, 4, 1234-1244;
96. c) Y. P. Dong, M. J. Shi, B. H. Tong, Q. F. Zhang, Luminescence 2012, 27, 414-418;
97. d) W. Yang, H. Fu, Q. Song, M. Zhang, Y. Ding, Organometallics 2011, 30, 77-83.