A metathesis model for the dehydrogenative coupling of amines with alcohols and esters into carboxamides by milsteins [Ru(PNN)(CO)(H)] catalysts

Inorganic Chemistry

Volumn 53, Issue 16, 2014, Pages 8334-8349

  Hasanayn, Faraj ^a   Harb, Hassan ^a  

^a AMERICAN UNIVERSITY OF BEIRUT   (Lebanon)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84906263260     PISSN: 00201669     EISSN: 1520510X     Source Type: Journal    
DOI: 10.1021/ic500743u     Document Type: Article

References (121)

1. Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 2005, 127, 10840
2. Zhang, J.; Balaraman, E.; Leitus, G.; Ben-David, Y.; Milstein, D. Organometallics 2011, 30, 5716
3. Gunanathan, C.; Ben-David, Y.; Milstein, D. Science 2007, 317, 790
4. Gunanathan, C.; Milstein, D. Angew. Chem., Int. Ed. 2008, 47, 8661
5. Khusnutdinova, J. R.; Ben-David, Y.; Milstein, D. Adv. Synth. Catal. 2013, 355, 3525
6. Zeng, H.; Guan, Z. J. Am. Chem. Soc. 2011, 133, 1159
7. Gnanaprakasam, B.; Balaraman, E.; Gunanathan, C.; Milstein, D. J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 1755
8. Gnanaprakasam, B.; Ben-David, Y.; Milstein, D. Adv. Synth. Catal. 2010, 352, 3169
9. Srimani, D.; Balaraman, E.; Gnanaprakasam, B.; Ben-David, Y.; Milstein, D.; Leitner, W. Adv. Synth. Catal. 2012, 354, 2403
10. Gnanaprakasam, B.; Milstein, D. J. Am. Chem. Soc. 2011, 133, 1682
11. Barrios-Francisco, R.; Balaraman, E.; Diskin-Posner, Y.; Leitus, G.; Shimon, L. J. W.; Milstein, D. Organometallics 2013, 32, 2973
12. Milstein, D. Top. Catalysis 2010, 53, 915
13. Gunanathan, C.; Milstein, D. Top. Organomet. Chem. 2011, 37, 55
14. Ito, M.; Ootsuka, T.; Watari, R.; Shibashi, A.; Himizu, A.; Ikariya, T. J. Am. Chem. Soc. 2011, 133, 4240
15. Dub, P. A.; Ikariya, T. ACS Catal. 2012, 2, 1718
16. Clarke, M. L. Catal. Sci. Technol. 2012, 2, 2418
17. Zeng, H.; Guan, Z. J. Am. Chem. Soc. 2011, 133, 1159
18. Gnanaprakasam, B.; Balaraman, E.; Gunanathan, C.; Milstein, D. J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 1755
19. Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2006, 45, 1113
20. Zell, T.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2014, 53, 4685
21. Balaraman, E.; Gnanaprakasam, B.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2010, 132, 16756
22. de Vries, J. G.; Elsevier, C. J. The Handbook of Homogeneous Hydrogenation; Wiley-VCH: Weinheim, Germany, 2007.
23. Noyori, R.; Hashiguchi, S. In Applied Homogeneous Catalysis with Organometallic Compounds; Wiley-VCH Verlag GmbH: New York, 2008.
24. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
25. Trost, B. M.; Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon, New York, 1991; Vol. 8.
26. Seyden-Penne, J. Reductions by the Alumino- and Borohydrides in Organic Synthesis, 2 nd ed.; Wiley: New York, 1997.
27. Gribble, G. W. Chem. Soc. Rev. 1998, 27, 395
28. Balaraman, E.; Gunanathan, C.; Zhang, J.; Shimon, L. J. W.; Milstein, D. Nat. Chem. 2011, 3, 609
29. Balaraman, E.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2011, 50, 11702
30. Ito, M.; Ootsuka, T.; Watari, R.; Shiibashi, A.; Himizu, A.; Ikariya, T. J. Am. Chem. Soc. 2011, 133, 4240
31. Dub, P. A.; Ikariya, T. ACS Catal. 2012, 2, 1718
32. Gunanathan, C.; Milstein, D. Acc. Chem. Res. 2011, 44, 588
33. Gunanathan, C.; Milstein, D. Science 2013, 341, 249
34. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97
35. Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008
36. Clapham, S. E.; Hadzovic, A.; Morris, R. H. Coord. Chem. Rev. 2004, 248, 2201
37. Joseph, S. M.; Samec, J. S.; Backvall, J.-E.; Andersson, P. G. Chem. Soc. Rev. 2006, 35, 237
38. Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681
39. Eisenstein, O.; Crabtree, R. H. New. J. Chem. 2013, 37, 21
40. Wiberg, K. B.; Morgan, K. M.; Maltz, H. J. Am. Chem. Soc. 1994, 116, 11067
41. Carey, F. A. Organic Chemistry, 6 th ed.; McGraw Hill Inc.: New York, 2006; Chapter 17.
42. Roundhill, D. M. Chem. Rev. 1992, 92, 1
43. Hamid, M. H. S. A.; Slatford, P. A.; Williams, J. M. J. Adv. Synth. Catal. 2007, 349, 1555
44. Fujita, K.; Fujii, T.; Yamaguchi, R. Org. Lett. 2004, 6, 3525
45. Yamaguchi, R.; Kawagoe, S.; Asai, C.; Fujita, K. Org. Lett. 2008, 10, 181
46. Tillack, A.; Hollmann, D.; Michalik, D.; Beller, M. Tetrahedron Lett. 2006, 47, 8881
47. Hollmann, D.; Tillack, A.; Michalik, D.; Jackstell, R.; Beller, M. Chem.-Asian J. 2007, 2, 403
48. Hamid, M. H. S. A.; Williams, J. M. J. Chem. Commun. 2007, 725
49. Balcells, D.; Nova, A.; Clot, E.; Gnanamgari, D.; Crabtree, R. H.; Eisenstein, O. Organometallics 2008, 27, 2529
50. Nova, A.; Balcells, D.; Dobereiner, G. H.; Crabtree, R. H.; Eisenstein, O. Organometallics 2010, 29, 6548
51. Gnanaprakasam; Zhang, J.; Milstein, D. Angew. Chem., Int. Ed. 2010, 49, 1468
52. Li, H.; Wang, X.; Huang, F.; Lu, G.; Jiang, J.; Wang, Z.-X. Organometallics 2011, 30, 5233
53. Li, H.; Wen, M.; Wang, Z. X. Inorg. Chem. 2012, 51, 5716
54. Li, H.; Wang, X.; Wen, M.; Wang, Z.-X. Eur. J. Inorg. Chem. 2012, 2012, 5011
55. Cho, D.; Ko, K. C.; Lee, J. Y. Organometallics 2013, 32, 4571
56. Qu, S.; Dang, Y.; Song, C.; Wen, M.; Huang, K.-W.; Wang, Z. J. Am. Chem. Soc. 2014, 136, 4947
57. Zeng, G.; Li, S. Inorg. Chem. 2011, 50, 10572
58. Cantillo, D. Eur. J. Inorg. Chem. 2011, 19, 3008
59. Iron, M. A.; Ben-Ari, E.; Cohen, R.; Milstein, D. Dalton Trans. 2009, 9433
60. Schwartsburd, L.; Iron, M. A.; Konstantinovski, L.; Diskin-Posner, Y.; Leitus, G.; Shimon, L. J. W.; Milstein, D. Organometallics 2010, 29, 3817
61. Tomasi, J.; Mennucci, B.; Cances, E. J. Mol. Struct. (THEOCHEM) 1999, 464, 211
62. Yang, X. ACS Catal. 2012, 2, 964
63. Yang, X. ACS Catal. 2013, 2684
64. Sandhya, K. S.; Suresh, C. H. Organometallics 2013, 32, 2926
65. Li, H.; Hall, M. B. J. Am. Chem. Soc. 2014, 136, 383
66. Basolo, F.; Pearson, R. G. Prog. Inorg. Chem. 1962, 4, 381
67. Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335
68. Coe, B. J.; Glenwright, S. J. Coord. Chem. Rev. 2000, 203, 5
69. Appleton, T. G.; Bennett, M. A. Inorg. Chem. 1978, 17, 738
70. Appleton, T. G.; Hall, J. R.; Ralph, S. F. Inorg. Chem. 1985, 24, 4685
71. Weinhold, F.; Landis, C. R. Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective; Cambridge University Press: Cambridge, 2005.
72. Hasanayn, F.; Abu-El-Ez, D. Inorg. Chem. 2010, 49, 9162
73. Hasanayn, F.; Achord, P.; Braunstein, P.; Magnier, H. J.; Krogh-Jespersen, K.; Goldman, A. S. Organometallics 2012, 31, 4680
74. Hasanayn, F.; Morris, R. H. Inorg. Chem. 2012, 51, 10808
75. Hasanayn, F.; Baroudi, A. Organometallics 2013, 32, 2493
76. Hasanayn, F.; Baroudi, A.; Bengali, A.; Goldman, A. S. Organometallics 2013, 32, 6969
77. Spasyuk, D.; Smith, S.; Gusev, D. G. Angew. Chem., Int. Ed. 2013, 52, 2538
78. Khaskin, E.; Iron, M. A.; Shimon, L. J. W.; Zhang, J.; Milstein, D. J. Am. Chem. Soc. 2010, 132, 8542
79. Frisch, M. J.. Gaussian 09, Rev. A.02; Gaussian, Inc.: Wallingford, CT, 2009.
80. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
81. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639
82. Raghavachari, K.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650
83. Rassolov, V. A.; Ratner, M. A.; Pople, J. A.; Redfern, P. C.; Curtiss, L. A. J. Comput. Chem. 2001, 22, 976
84. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 279
85. Höllwarth, A.; Böhlers, A. W.; Bohme, M.; Dapprich, S.; Gobbi, A.; Hollwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111
86. See: https://bse.pnl.gov/bse/portal.
87. Fukui, K. Acc. Chem. Res. 1981, 14, 363
88. Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, 194101
89. Chai, J.-D.; Head-Gordon, M. Phys. Chem. Chem. Phys. 2008, 10, 6615
90. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378
91. Averkiev, B. B.; Truhlar, D. G. Catal. Sci. Technol. 2011, 1, 1526
92. Gusev, D. G. Organometallics 2013, 32, 4239
93. Pudasaini, B.; Janesko, B. J. Organometallics 2014, 33, 84
94. Remya, K.; Suresh, C. H. J. Comput. Chem. 2013, 34, 1341
95. Yang, X. Inorg. Chem. 2011, 50, 12836
96. Sandoval, C. A.; Ohkuma, T.; Muñiz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490
97. Casey, C. P.; Johnson, J. B.; Singer, S. W.; Cui, Q. J. Am. Chem. Soc. 2005, 127, 3100
98. Hedberg, C.; Kallstrom, K.; Arvidsson, P. I.; Brandt, P.; Andersson, P. G. J. Am. Chem. Soc. 2005, 127, 15083
99. Xin Zhang, X.; Guo, X.; Chen, Y.; Tang, Y.; Lei, M.; Fang, W. Phys. Chem. Chem. Phys. 2012, 14, 6003
100. Findlater, M.; Bernskoetter, W. H.; Brookhart, M. J. Am. Chem. Soc. 2010, 132, 4534
101. Takebayashi, S.; Bergens, S. H. Organometallics 2009, 28, 2349
102. Baratta, W.; Chelucci, G.; Gladiali, S.; Siega, K.; Toniutti, M.; Zanette, M.; Zangrando, E.; Rigo, P. Angew. Chem., Int. Ed. 2005, 44, 6214
103. Baratta, W.; Bosco, M.; Chelucci, G.; Del Zotto, A.; Siega, K.; Toniutti, M.; Zangrando, E.; Rigo, P. Organometallics 2006, 25, 4611
104. Baratta, W.; Ballico, M.; Esposito, G.; Rigo, P. Chem.-Eur. J. 2008, 14, 558
105. Hamilton, R. J.; Leong, C. G.; Bigam, G.; Miskolzie, M.; Bergens, S. H. J. Am. Chem. Soc. 2005, 127, 4152
106. Hamilton, R. J.; Bergens, S. H. J. Am. Chem. Soc. 2006, 128, 13700
107. Hamilton, R. J.; Bergens, S. H. J. Am. Chem. Soc. 2008, 130, 11979
108. Takebayashi, S.; Dabral, N.; Miskolzie, M.; Bergens, S. H. J. Am. Chem. Soc. 2011, 133, 9666
109. Bertoli, M.; Choualeb, A.; Lough, A. J.; Moore, B.; Spasyuk, D.; Gusev, D. G. Organometallics 2011, 30, 3479
110. Spasyuk, D.; Gusev, D. G. Organometallics 2012, 31, 5239
111. Darensbourg, D. J.; Rokicki, A.; Darensbourg, M. Y. J. Am. Chem. Soc. 1981, 103, 3223
112. Darensbourg, D. J.; Kudaroski, R.; Bauch, C. G.; Pala, M.; Simmons, D.; White, J. N. J. Am. Chem. Soc. 1985, 107, 7463
113. Darensbourg, D. J.; Kyran, S. J.; Yeung, A. D.; Bengali, A. A. Eur. J. Inorg. Chem. 2013, 4024
114. Whittlesey, M. K.; Perutz, R. N.; Moore, M. H. Organometallics 1996, 15, 5166
115. Salem, H.; Shimon, L. J. W.; Diskin-Posner, Y.; Leitus, G.; Ben-David, Y.; Milstein, D. Organometallics 2009, 28, 4791
116. Langer, R.; Diskin-Posner, Y.; Leitus, G.; Shimon, L. J. W.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2011, 50, 9948
117. Schmeier, T. J.; Dobereiner, G. E.; Crabtree, R. H.; Hazari, N. J. Am. Chem. Soc. 2011, 133, 9274
118. Blum, O.; Milstein, D. J. Organomet. Chem. 2000, 593-594, 479
119. Smythe, N. A.; Grice, K. A.; Williams, B. S.; Goldberg, K. I. Organometallics 2009, 28, 277
120. Fafard, C. M.; Ozerov, O. V. Inorg. Chim. Acta 2007, 360, 286
121. Handgraaf, J.-W.; Meijer, E. J. J. Am. Chem. Soc. 2007, 129, 3099