Ruthenium-catalyzed N-alkylation of amines with alcohols under mild conditions using the borrowing hydrogen methodology

Journal of Organic Chemistry

Volumn 79, Issue 16, 2014, Pages 7553-7563

  Enyong, Arrey B ^a   Moasser, Bahram ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSIS; RUTHENIUM;

AMIDE LIGANDS; BORROWING HYDROGENS; HIGH CONVERSIONS; HIGH SELECTIVITY; HIGH TEMPERATURE; PRIMARY AND SECONDARY AMINE; ROOM TEMPERATURE; SIMPLE ALCOHOLS;

ALKYLATION;

ALCOHOL; ALCOHOL DERIVATIVE; ALDEHYDE; ALIPHATIC AMINE; ALKANOL; AMINE; ANILINE; BENZALDEHYDE; BENZYL ALCOHOL; HYDROGEN; PHENETHYLAMINE; RUTHENIUM; TOLUENE; LIGAND; SOLVENT;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; DEHYDROGENATION; HIGH TEMPERATURE; NUCLEOPHILICITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; ROOM TEMPERATURE; STOICHIOMETRY; CHEMICAL STRUCTURE; CHEMISTRY;

ALCOHOLS; ALKYLATION; AMINES; CATALYSIS; HYDROGEN; LIGANDS; MOLECULAR STRUCTURE; RUTHENIUM; SOLVENTS;

EID: 84906100058     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501273t     Document Type: Article

References (96)

1. Romera, J. L.; Cid, J. M.; Trabanco, A. A. Tetrahedron Lett. 2004, 45, 8797
2. Salvatore, R. N.; Nagle, A. S.; Jung, K. W. J. Org. Chem. 2002, 67, 674
3. Salvatore, R. N.; Yoon, C. H.; Jung, K. W. Tetrahedron 2001, 57, 7785
4. Singh, C. B.; Kavala, V.; Samal, A. K.; Patel, B. K. Eur. J. Org. Chem. 2007, 2007, 1369
5. Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84
6. Tararov, V. I.; Borner, A. Synlett 2005, 203
7. Bähn, S.; Imm, S.; Neubert, L.; Zhang, M.; Neumann, H.; Beller, M. ChemCatChem 2011, 3, 1853
8. Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681
9. Guillena, G.; Ramon, D. J.; Yus, M. Chem. Rev. 2010, 110, 1611
10. Hamid, M. H. S. A.; Slatford, P. A.; Williams, J. M. J. Adv. Synth. Catal. 2007, 349, 1555
11. Nixon, T. D.; Whittlesey, M. K.; Williams, J. M. Dalton Trans. 2009, 753
12. Li, C. J.; Trost, B. M. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 13197
13. Grigg, R.; Mitchell, T. R. B.; Sutthivaiyakit, S.; Tongpenyai, N. J. Chem. Soc., Chem. Commun. 1981, 611
14. Tsuji, Y.; Huh, K. T.; Ohsugi, Y.; Watanabe, Y. J. Org. Chem. 1985, 50, 1365
15. Watanabe, Y.; Morisaki, Y.; Kondo, T.; Mitsudo, T. J. Org. Chem. 1996, 61, 4214
16. Watanabe, Y.; Tsuji, Y.; Ige, H.; Ohsugi, Y.; Ohta, T. J. Org. Chem. 1984, 49, 3359
17. Watanabe, Y.; Tsuji, Y.; Ohsugi, Y. Tetrahedron Lett. 1981, 22, 2667
18. Fujita, K.; Fujii, T.; Komatsubara, A.; Enoki, Y.; Yamaguchi, R. Heterocycles 2007, 74, 673
19. Fujita, K.; Kida, Y.; Yamaguchi, R. Heterocycles 2009, 77, 1371
20. Fujita, K. I.; Fujii, T.; Yamaguchi, R. Org. Lett. 2004, 6, 3525
21. Fujita, K.-i.; Enoki, Y.; Yamaguchi, R. Tetrahedron 2008, 64, 1943
22. Fujita, K.-i.; Li, Z.; Ozeki, N.; Yamaguchi, R. Tetrahedron Lett. 2003, 44, 2687
23. Fujita, K.-i.; Yamaguchi, R.; Mingwen, Z.; Kawagoe, S.; Asai, C. Synthesis 2009, 2009, 1220
24. Kawahara, R.; Fujita, K.; Yamaguchi, R. J. Am. Chem. Soc. 2010, 132, 15108
25. Kawahara, R.; Fujita, K.-i.; Yamaguchi, R. Adv. Synth. Catal. 2011, 353, 1161
26. Yamaguchi, R.; Fujita, K.-i. Synlett 2005, 560
27. Yamaguchi, R.; Kawagoe, S.; Asai, C.; Fujita, K. I. Org. Lett. 2008, 10, 181
28. Zhu, M. W.; Fujita, K.; Yamaguchi, R. Org. Lett. 2010, 12, 1336
29. Bahn, S.; Imm, S.; Mevius, K.; Neubert, L.; Tillack, A.; Williams, J. M.; Beller, M. Chemistry 2010, 16, 3590
30. Cami-Kobeci, G.; Slatford, P. A.; Whittlesey, M. K.; Williams, J. M. Bioorg. Med. Chem. Lett. 2005, 15, 535
31. Cami-Kobeci, G.; Williams, J. M. Chem. Commun. 2004, 1072
32. Hamid, M. H.; Williams, J. M. Chem. Commun. 2007, 725
33. Hamid, M. H. S. A.; Williams, J. M. J. Tetrahedron Lett. 2007, 48, 8263
34. Lamb, G. W.; Al Badran, F. A.; Williams, J. M. J.; Kolaczkowski, S. T. Chem. Eng. Res. Des. 2010, 88, 1533
35. Lamb, G. W.; Watson, A. J. A.; Jolley, K. E.; Maxwell, A. C.; Williams, J. M. J. Tetrahedron Lett. 2009, 50, 3374
36. Saidi, O.; Blacker, A. J.; Farah, M. M.; Marsden, S. P.; Williams, J. M. Chem. Commun. 2010, 46, 1541
37. Watson, A. J.; Maxwell, A. C.; Williams, J. M. J. Org. Chem. 2011, 76, 2328
38. Ma, W. M. J.; James, T. D.; Williams, J. M. J. Org. Lett. 2013, 15, 4850
39. Martinez-Asencio, A.; Ramon, D. J.; Yus, M. Tetrahedron Lett. 2010, 51, 325
40. Martinez-Asencio, A.; Ramon, D. J.; Yus, M. Tetrahedron 2011, 67, 3140
41. Martinez-Asencio, A.; Yus, M.; Ramon, D. J. Synthesis-Stuttgart 2011, 3730
42. Bahn, S.; Tillack, A.; Imm, S.; Mevius, K.; Michalik, D.; Hollmann, D.; Neubert, L.; Beller, M. ChemSusChem 2009, 2, 551
43. Hollmann, D.; Tillack, A.; Michalik, D.; Jackstell, R.; Beller, M. Chem.-Asian J. 2007, 2, 403
44. Imm, S.; Bahn, S.; Neubert, L.; Neumann, H.; Beller, M. Angew. Chem. 2010, 49, 8126
45. Imm, S.; Bähn, S.; Zhang, M.; Neubert, L.; Neumann, H.; Klasovsky, F.; Pfeffer, J.; Haas, T.; Beller, M. Angew. Chem., Int. Ed. 2011, 50, 7599
46. Tillack, A.; Hollmann, D.; Mevius, K.; Michalik, D.; Bähn, S.; Beller, M. Eur. J. Org. Chem. 2008, 2008, 4745
47. Tillack, A.; Hollmann, D.; Michalik, D.; Beller, M. Tetrahedron Lett. 2006, 47, 8881
48. Blank, B.; Madalska, M.; Kempe, R. Adv. Synth. Catal. 2008, 350, 749
49. Blank, B.; Michlik, S.; Kempe, R. Chemistry 2009, 15, 3790
50. Blank, B. t.; Michlik, S.; Kempe, R. Adv. Synth. Catal. 2009, 351, 2903
51. Michlik, S.; Kempe, R. Chemistry 2010, 16, 13193
52. Bartoszewicz, A.; Marcos, R.; Sahoo, S.; Inge, A. K.; Zou, X.; Martín-Matute, B. Chem.-Eur. J. 2012, 18, 14510
53. Li, J.-Q.; Andersson, P. G. Chem. Commun. 2013, 49, 6131
54. Andrushko, N.; Andrushko, V.; Roose, P.; Moonen, K.; Börner, A. ChemCatChem 2010, 2, 640
55. Berliner, M. A.; Dubant, S. p. P. A.; Makowski, T.; Ng, K.; Sitter, B.; Wager, C.; Zhang, Y. Org. Process Res. Dev. 2011, 15, 1052
56. Chang, Y. H.; Fu, C. F.; Liu, Y. H.; Peng, S. M.; Chen, J. T.; Liu, S. T. Dalton Trans. 2009, 861
57. Cumpstey, I.; Agrawal, S.; Borbas, K. E.; Martin-Matute, B. Chem. Commun. 2011, 47, 7827
58. da Costa, A. P.; Sanau, M.; Peris, E.; Royo, B. Dalton Trans. 2009, 6960
59. Gnanamgari, D.; Sauer, E. L. O.; Schley, N. D.; Butler, C.; Incarvito, C. D.; Crabtree, R. H. Organometallics 2008, 28, 321
60. Li, F.; Shan, H.; Chen, L.; Kang, Q.; Zou, P. Chem. Commun. 2012, 48, 603
61. Ohta, H.; Yuyama, Y.; Uozumi, Y.; Yamada, Y. M. A. Org. Lett. 2011, 13, 3892
62. Prades, A.; Corberan, R.; Poyatos, M.; Peris, E. Chemistry 2008, 14, 11474
63. Wetzel, A.; Wöckel, S.; Schelwies, M.; Brinks, M. K.; Rominger, F.; Hofmann, P.; Limbach, M. Org. Lett. 2013, 15, 266
64. Zhang, W.; Dong, X.; Zhao, W. Org. Lett. 2011, 13, 5386
65. Agrawal, S.; Lenormand, M.; Martín-Matute, B. Org. Lett. 2012, 14, 1456
66. Del Zotto, A.; Baratta, W.; Sandri, M.; Verardo, G.; Rigo, P. Eur. J. Org. Chem. 2004, 2004, 524
67. Fernández, F. E.; Puerta, M. C.; Valerga, P. Organometallics 2012, 31, 6868
68. Gunanathan, C.; Milstein, D. Angew. Chem., Int. Ed. 2008, 47, 8661
69. Pingen, D.; Müller, C.; Vogt, D. Angew. Chem., Int. Ed. 2010, 49, 8130
70. Weickmann, D.; Frey, W.; Plietker, B. Chem.-Eur. J. 2013, 19, 2741
71. Bertoli, M.; Choualeb, A.; Lough, A. J.; Moore, B.; Spasyuk, D.; Gusev, D. G. Organometallics 2011, 30, 3479
72. Cui, X.; Shi, F.; Tse, M. K.; Gördes, D.; Thurow, K.; Beller, M.; Deng, Y. Adv. Synth. Catal. 2009, 351, 2949
73. Dixit, M.; Mishra, M.; Joshi, P. A.; Shah, D. O. Catal. Commun. 2013, 33, 80
74. Likhar, P. R.; Arundhathi, R.; Kantam, M. L.; Prathima, P. S. Eur. J. Org. Chem. 2009, 2009, 5383
75. Martínez-Asencio, A.; Ramón, D. J.; Yus, M. Tetrahedron 2011, 67, 3140
76. Shi, F.; Tse, M. K.; Cui, X.; Gordes, D.; Michalik, D.; Thurow, K.; Deng, Y.; Beller, M. Angew. Chem. 2009, 48, 5912
77. Zotova, N.; Roberts, F. J.; Kelsall, G. H.; Jessiman, A. S.; Hellgardt, K.; Hii, K. K. Green Chem. 2012, 14, 226
78. Martinez, R.; Ramon, D. J.; Yus, M. Org. Biomol. Chem. 2009, 7, 2176
79. Cui, X.; Zhang, Y.; Shi, F.; Deng, Y. Chem.-Eur. J. 2011, 17, 1021
80. Liu, H.; Chuah, G.-K.; Jaenicke, S. J. Catal. 2012, 292, 130
81. Shimizu, K.; Nishimura, M.; Satsuma, A. ChemCatChem 2009, 1, 497
82. Shimizu, K.-i.; Shimura, K.; Nishimura, M.; Satsuma, A. RSC Adv. 2011, 1, 1310
83. Dang, T. T.; Ramalingam, B.; Shan, S. P.; Seayad, A. M. ACS Catal. 2013, 3, 2536
84. Pelagatti, P.; Carcelli, M.; Calbiani, F.; Cassi, C.; Elviri, L.; Pelizzi, C.; Rizzotti, U.; Rogolino, D. Organometallics 2005, 24, 5836
85. Wu, Z.; Zhou, L.; Jiang, Z.; Wu, D.; Li, Z.; Zhou, X. Eur. J. Org. Chem. 2010, 2010, 4971
86. Cavezza, A.; Rozot, R.; Use of Piperidine Derivatives as Dermocontracting Agents US Patent 7629358 B2, Dec. 8, 2009.
87. Ikawa, T.; Fujita, Y.; Mizusaki, T.; Betsuin, S.; Takamatsu, H.; Maegawa, T.; Monguchi, Y.; Sajiki, H. Org. Biomol. Chem. 2012, 10, 293
88. Garashchenko, Z. M.; Domnina, E. S.; Afonin, A. V. Russ. J. Gen. Chem. 1996, 66, 975
89. Cai, J.; Wathey, B. Tetrahedron Lett. 2001, 42, 1383
90. Liu, B.; Roisnel, T.; Carpentier, J.-F.; Sarazin, Y. Angew. Chem., Int. Ed. 2012, 51, 4943
91. Du, Y.; Oishi, S.; Saito, S. Chem.-Eur. J. 2011, 17, 12262
92. Hollmann, D.; Bähn, S.; Tillack, A.; Beller, M. Angew. Chem., Int. Ed. 2007, 46, 8291
93. Yung-Son, H.; Ling, L. Tetrahedron Lett. 1993, 34, 5309
94. McGonagle, F. I.; MacMillan, D. S.; Murray, J.; Sneddon, H. F.; Jamieson, C.; Watson, A. J. B. Green Chem. 2013, 15, 1159
95. Kuwano, R.; Kondo, Y.; Matsuyama, Y. J. Am. Chem. Soc. 2003, 125, 12104
96. Sharma, S. K.; Lynch, J.; Sobolewska, A. M.; Plucinski, P.; Watson, R. J.; Williams, J. M. J. Catal. Sci. Technol. 2013, 3, 85