N-H activation by Rh(I) via metal-ligand cooperation

Organometallics

Volumn 31, Issue 11, 2012, Pages 4083-4101

  Feller, Moran ^a   Diskin Posner, Yael ^a   Shimon, Linda J W ^a   Ben Ari, Eyal ^a   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION RATES; ANCILLARY LIGANDS; ANIONIC COMPLEX; ASSOCIATIVE MECHANISMS; BOND ACTIVATION; CHEMICAL EXCHANGE; CYCLOOCTENE; ELECTRON WITHDRAWING GROUP; METAL CENTERS; N-H ACTIVATION; OXIDATION STATE; PENTACOORDINATED; PINCER COMPLEXES; PINCER LIGANDS; RH COMPLEXES; SATURATION TRANSFER;

ANILINE; BIOACTIVITY; BROMINE; CHEMICAL BONDS; CHLORINE; CHLORINE COMPOUNDS; ETHYLENE; LIGANDS; METALS; NITROGEN OXIDES; RHODIUM;

RHODIUM COMPOUNDS;

EID: 84862137636     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om300248r     Document Type: Article

References (128)

1. Gunanathan, C.; Milstein, D. Acc. Chem. Res. 2011, 44, 588
2. Gunanathan, C.; Milstein, D. Top. Organomet. Chem 2011, 37, 55
3. Milstein, D. Top. Catal 2010, 53, 915
4. van der Vlugt, J. L.; Reek, J. N. H. Angew. Chem., Int. Ed. 2009, 48, 8832
5. Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 2005, 127, 10840
6. Zhang, J.; Gandelman, M.; Shimon, L. J. W.; Milstein, D. Dalton Trans. 2007, 107
7. Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2006, 45, 1113
8. Gunanathan, C.; Ben-David, Y.; Milstein, D. Science 2007, 317, 790
9. Gnanaprakasam, B.; Ben-David, Y.; Milstein, D. Adv. Synth. Catal. 2010, 352, 3169
10. Gnanaprakasam, B.; Milstein, D. J. Am. Chem. Soc. 2011, 133, 1682
11. Balaraman, E.; Gunanathan, C.; Zhang, J.; Shimon, L. J. W.; Milstein, D. Nat. Chem. 2011, 3, 609
12. Zhang, J.; Balaraman, E.; Leitus, G.; Milstein, D. Organometallics 2011, 30, 5716
13. Gnanaprakasam, B.; Balaraman, E.; Gunanathan, C.; Milstein, D. J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 1755
14. Balaraman, E.; Gnanaprakasam, B.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2010, 132, 16756
15. Balaraman, E.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2011, 50, 11702
16. Balaraman, E.; Fogler, E.; Milstein, D. Chem. Commun. 2012, 48, 1111
17. Zhang, J.; Gandelman, M.; Shimon, L. J. W.; Rozenberg, H.; Milstein, D. Organometallics 2004, 23, 4026
18. Gnanaprakasam, B.; Zhang, J.; Milstein, D. Angew. Chem., Int. Ed. 2010, 49, 1468
19. Gunanathan, C.; Gnanaprakasam, B.; Iron, M. A.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2010, 132, 14763
20. Gunanathan, C.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2009, 131, 3146
21. Gunanathan, C.; Milstein, D. Angew. Chem., Int. Ed. 2008, 47, 8661
22. Langer, R.; Leitus, G.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2011, 50, 2120
23. Langer, R.; Diskin-Posner, Y.; Leitus, G.; Shimon, L. J. W.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2011, 50, 9948
24. Langer, R.; Iron, M. A.; Konstantinovski, L.; Diskin-Posner, Y.; Leitus, G.; Ben-David, Y.; Milstein, D. Chem.-Eur. J. 2012. DOI: 10.1002/chem.201200159.
25. Fogler, E.; Balaraman, E.; Ben-David, Y.; Leitus, G.; Shimon, L. J. W.; Milstein, D. Organometallics 2011, 30, 3826
26. Zeng, H.; Guan, Z. J. Am. Chem. Soc. 2011, 133, 1159
27. Gnanaprakasam, B.; Balaraman, E.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2011, 50, 12240
28. Hunsicker, D. M.; Dauphinais, B. C.; McIlrath, S. P.; Robertson, N. J. Macromol. Rapid Commun. 2012, 33, 232
29. Zeng, G.; Li, S. Inorg. Chem. 2011, 50, 10572
30. Li, H.; Wang, X.; Huang, F.; Lu, G.; Jiang, J.; Wang, Z.-X. Organometallics 2011, 30, 5233
31. Sandhya, K. S.; Suresh, C. H. Organometallics 2011, 30, 3888
32. Cantillo, D. Eur. J. Inorg. Chem. 2011, 19, 3008
33. Yang, X. Inorg. Chem. 2011, 50, 12836
34. Rigoli, J. W.; Moyer, S. A.; Pearce, S. D.; Schomaker, J. M. Org. Biomol. Chem. 2012, 10, 1746
35. He, L.-P.; Chen, T.; Xue, D.-X.; Eddaoudi, M.; Huang, K.-W. J. Organomet. Chem. 2012, 700, 202
36. Huff, C. A.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18122
37. Sun, Y.; Koehler, C.; Tan, R.; Annibale, V. T.; Song, D. Chem. Commun. 2011, 47, 8349
38. del Pozo, C.; Iglesias, M.; Sanchez, F. Organometallics 2011, 30, 2180
39. Staubitz, A.; Sloan, M. E.; Robertson, A. P. M.; Friedrich, A.; Schneider, S.; Gates, P. J.; Schmedt auf der Gunne, J.; Manners, I. J. Am. Chem. Soc. 2010, 132, 13332
40. van der Vlugt, J. I.; Lutz, M.; Pidko, E. A.; Vogt, D.; Spek, A. L. Dalton Trans. 2009, 6, 1016
41. Tanaka, R.; Yamashita, M.; Nozaki, K. J. Am. Chem. Soc. 2009, 131, 14168
42. Ben Ari, E.; Leitus, G.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2006, 128, 15390
43. Schwartsburd, L.; Iron, M. A.; Konstantinovski, L.; Diskin-Posner, Y.; Leitus, G.; Shimon, L. J. W.; Milstein, D. Organometallics 2010, 29, 3817
44. Iron, M. A.; Ben-Ari, E.; Cohen, R.; Milstein, D. Dalton Trans. 2009, 9433
45. Zeng, G.; Guo, Y.; Li, S. Inorg. Chem. 2009, 48, 10257
46. Schwartsburd, L.; Iron, M. A.; Konstantinovski, L.; Ben-Ari, E.; Milstein, D. Organometallics 2011, 30, 2721
47. Kohl, S. W.; Weiner, L.; Schwartsburd, L.; Konstantinovski, L.; Shimon, L. J. W.; Ben-David, Y.; Iron, M. A.; Milstein, D. Science 2009, 324, 74
48. Lawrence, S. A. Amines: Synthesis, Properties and Applications; Cambridge University Press: Cambridge, U.K., 2004.
49. Roundhill, D. M. Chem. Rev. 1992, 92, 1
50. Klinkenberg, J. L.; Hartwig, J. F. Angew. Chem., Int. Ed. 2011, 50, 86
51. van der Vlugt, J. I. Chem. Soc. Rev. 2010, 39, 2302
52. Enthaler, S. ChemSusChem 2010, 3, 1024
53. Müller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795
54. Hartwig, J. F. Pure Appl. Chem. 2004, 76, 507
55. Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675
56. Eilbracht, P.; Baerfacker, L.; Buss, C.; Hollmann, C.; Kitsos-Rzychon, B. E.; Kranemann, C. L.; Rische, T.; Roggenbuck, R.; Schmidt, A. Chem. Rev. 1999, 99, 3329
57. Eilbracht, P.; Schmidt, A. M. Top. Organomet. Chem. 2006, 18, 65
58. Sadig, J. E. R.; Willis, M. C. Synthesis 2011, 1, 1
59. Aubin, Y.; Fischmeister, C.; Thomas, C. M.; Jean-Luc, R. Chem. Soc. Rev. 2010, 39, 413
60. Enthaler, S. ChemSusChem 2010, 3, 1024
61. Gillespie, J. A.; Dodds, D. L.; Kamer, P. C. J. Dalton Trans. 2010, 39, 2751
62. Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84
63. Nugent, T. C.; El-Shazly, M. Adv. Synth. Catal. 2010, 352, 753
64. Gomez, S.; Peters, J. A.; Maschmeyer, T. Adv. Synth. Catal. 2002, 344, 1037
65. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069
66. Grey, R. A.; Pez, G. P.; Wallo, A. J. Am. Chem. Soc. 1981, 103, 7536
67. Suarez, T.; Fontal, B. J. Mol. Catal. 1988, 45, 335
68. Mukherjee, D. K.; Palit, B. K.; Saha, C. R. J. Mol. Catal. 1994, 88, 57
69. Takemoto, S.; Kawamura, H.; Yamada, Y.; Okada, T. Organometallics 2002, 21, 3897
70. Enthaler, S.; Addis, D.; Junge, K.; Erre, G.; Beller, M. Chem.-Eur. J. 2008, 14, 9491
71. Enthaler, S.; Junge, K.; Addis, D.; Erre, G.; Beller, M. ChemSusChem 2008, 1, 1006
72. Addis, D.; Enthaler, S.; Junge, K.; Wendt, B.; Beller, M. Tetrahedron Lett. 2009, 50, 3654
73. Chin, C. S.; Lee, B. Catal. Lett. 1992, 14, 135
74. Zerecero-Silva, P.; Jimenez-Solar, I.; Crestani, M. G.; Arévalo, A.; Barrios-Francisco, R.; García, J. J. Appl. Catal., A 2009, 363, 230
75. Yoshida, T.; Okano, T.; Otsuka, S. J. Chem. Soc., Chem. Commun. 1979, 870
76. Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738
77. Ir(I)-catalyzed asymmetric hydroamination: Dorta, R.; Egli, P.; Zucher, F.; Togni, A. J. Am. Chem. Soc. 1997, 119, 10857
78. Sappa, E.; Milone, L. J. Organomet. Chem. 1973, 61, 383
79. Ladipo, F. T.; Merola, J. S. Inorg. Chem. 1990, 29, 4172
80. Kanzelberger, M.; Zhang, X.; Emge, T. J.; Goldman, A. S.; Zhao, J.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 13644
81. Cartwright Sykes, A.; White, P.; Brookhart, M. Organometallics 2006, 25, 1664
82. Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. Organometallics 1991, 10, 1875
83. Fulton, J. R.; Holland, A. W.; Fox, D. J.; Bergman, R. G. Acc. Chem. Res. 2002, 35, 44
84. Pavlik, S.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 2003, 22, 1771
85. Grotjahn, D. B.; Gong, Y.; DiPasquale, A. G.; Zakharov, L. N.; Rheingold, A. L. Organometallics 2006, 25, 5693
86. Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. Inorg. Chem. 1987, 26, 971
87. Koelliker, R.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 707
88. Schulz, M.; Milstein, D. J. Chem. Soc., Chem. Commun. 1993, 318
89. Zhao, J.; Goldman, A. S.; Hartwig, J. F. Science 2005, 307, 1080
90. Huang, Z.; Zhou, J. S.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 11458
91. Morgan, E.; MacLean, D. F.; McDonald, R.; Turculet, L. J. Am. Chem. Soc. 2009, 131, 14234
92. Fafard, C. M.; Adhikari, D.; Foxman, B. M.; Mindiola, D. J.; Ozerov, O. V. J. Am. Chem. Soc. 2007, 129, 10318
93. Mena, I.; Casado, M. A.; Garcia-Orduna, P.; Polo, V.; Lahoz, F. J.; Fazal, A.; Oro, L. A. Angew. Chem., Int. Ed. 2011, 50, 11735
94. Khaskin, E.; Iron, M. A.; Shimon, L. J. W.; Zhang, J.; Milstein, D. J. Am. Chem. Soc. 2010, 132, 8542
95. Muniz, K.; Lishchynskyi, A.; Streuff, J.; Nieger, M.; Escudero-Adan, E. C.; Belmonte, M. M. Chem. Commun. 2011, 47, 4911
96. Gandelman, M.; Konstantinovski, L.; Rozenberg, H.; Milstein, D. Chem.-Eur. J. 2003, 9, 2595
97. Feller, M.; Ben-Ari, E.; Iron, M. A.; Diskin-Posner, Y.; Leitus, G.; Shimon, L. J. W.; Konstantinovski, L.; Milstein, D. Inorg. Chem. 2010, 49, 1615
98. Frech, C. M.; Shimon, L. J. W.; Milstein, D. Organometallics 2009, 28, 1900
99. Majumdar, M.; Patra, S. K.; Kannan, M.; Dunbar, K. R.; Bera, J. K. Inorg. Chem. 2008, 47, 2212
100. Drabent, K.; Clunlk, Z.; Ozarowskl, A. Inorg. Chem. 2008, 47, 3358
101. Feller, M.; Ben-Ari, E.; Gupta, T.; Shimon, L. J. W.; Leitus, G.; Diskin- Posner, Y.; Weiner, L.; Milstein, D. Inorg. Chem. 2007, 46, 10479
102. Salem, H.; Ben-David, Y.; Shimon, L. J. W.; Milstein, D. Organometallics 2006, 25, 2292
103. Frech, C. M.; Milstein, D. J. Am. Chem. Soc. 2006, 128, 12434
104. Rybtchinski, B.; Oevers, S.; Montag, M.; Vigalok, A.; Rozenberg, H.; Martin, J. M. L.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 9064
105. Beck, W.; Sunkel, K. Chem. Rev. 1988, 88, 1405
106. Sutherland, B. R.; Cowie, M. Inorg. Chem. 1984, 23, 1290
107. MacKay, B. A.; Fryzuk, M. D. Chem. Rev. 2004, 104, 385
108. Hermann, D.; Gandelman, M.; Rozenberg, H.; Shimon, L. J. W.; Milstein, D. Organometallics 2002, 21, 812
109. 1H} NMR spectra are lacking P-H coupling, presumably because of rapid rotation. See: Cramer, R. J. Am. Chem. Soc. 1964, 86, 217
110. The C=C bond length in free gaseous ethylene is estimated to be 1.3305(10) Å. Craig, N. C.; Groner, P.; McKean, D. C. J. Phys. Chem. A 2006, 110, 7461
111. The C=C bond length from X-ray data is 1.313 Å. Van Nes, G. J. H.; Vos, A. Acta Crystallogr., Sect. B 1979, 35, 2593
112. Feller, M.; Iron, A. M.; Shimon, L. J. W.; Diskin-Posner, Y.; Leitus, G.; Milstein, D. J. Am. Chem. Soc. 2008, 130, 14374
113. Hanson, S. K.; Heinekey, D. M.; Goldberg, K. I. Angew. Chem., Int. Ed. 2007, 46, 4736
114. Hanson, S. K.; Heinekey, D. M.; Goldberg, K. I. Organometallics 2008, 27, 1454
115. Tejel, C.; Ciriano, M. A.; Bordonaba, M.; López, J. A.; Lahoz, F. J.; Oro, L. A. Inorg. Chem. 2002, 41, 2348
116. Tejel, C.; Ciriano, M. A.; Bordonaba, M.; López, J. A.; Lahoz, F. J.; Oro, L. A. Chem.-Eur. J. 2002, 8, 3128
117. Fandos, R.; Martínez-Ripoll, M.; Otero, A.; Ruiz, M. J.; Rodríguez, A.; Terreros, P. Organometallics 1998, 17, 1465
118. Jarek, R. L.; Flesher, R. J.; Shin, S. K. J. Chem. Educ. 1997, 74, 978
119. Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1665
120. Vigalok, A.; Kraatz, H.-B.; Konstantinovski, L.; Milstein, D. Chem.-Eur. J. 1997, 3, 253
121. Rybtchinski, B.; Konstantinovski, L.; Shimon, L. J. W.; Vigalok, A.; Milstein, D. Chem.-Eur. J. 2000, 6, 3287
122. Montag, M.; Schwartsburd, L.; Cohen, R.; Leitus, G.; Ben-David, Y.; Martin, J. M. L.; Milstein, D. Angew. Chem., Int. Ed. 2007, 46, 1901
123. Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931
124. Vuzman, D.; Poverenov, E.; Shimon, L. J. W.; Diskin-Posner, Y.; Milstein, D. Organometallics 2008, 27, 2627
125. Feller, M.; Ben-Ari, E.; Iron, M. A.; Diskin-Posner, Y.; Leitus, G.; Shimon, L. J. W.; Konstantinovski, L.; Milstein, D. Inorg. Chem. 2010, 49, 1615 and references therein
126. Jansen, A.; Pitter, S. Monatsh. Chem. 1999, 130, 783
127. van der Ent, A.; Onderdelinden, A. L. Inorg. Synth. 1990, 28, 90
128. Cramer, R. Inorg. Synth. 1990, 28, 86