Intramolecular Hydroamination Reactions Catalyzed by Neutral and Cationic Group IV Pyridylamido Complexes

ChemCatChem

Volumn 5, Issue 5, 2013, Pages 1142-1151

  Luconi, Lapo ^a   Rossin, Andrea ^a   Tuci, Giulia ^a   Germain, Stéphane ^b   Schulz, Emmanuelle ^b,c   Hannedouche, Jérôme ^b,c   Giambastiani, Giuliano ^a  

^a CNR   (Italy)

^b UNIVERSITÉ PARIS SACLAY   (France)

^c CNRS   (France)

Author keywords

Cations; Hafnium; Hydroamination; Nitrogen heterocycles; Zirconium

Indexed keywords

CATALYTIC TRANSFORMATION; CATIONIC GROUPS; HETEROCYCLES; HYDROAMINATIONS; INTRAMOLECULAR HYDROAMINATION; METAL COORDINATION SPHERES; NITROGEN HETEROCYCLES; PRODUCTION OF;

AMINATION; HAFNIUM; HAFNIUM COMPOUNDS; POSITIVE IONS; ZIRCONIUM;

ZIRCONIUM COMPOUNDS;

EID: 84877012350     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201200389     Document Type: Article

References (139)

1. For a comprehensive review on the topic see: G. Giambastiani, L. Luconi, R. L. Kuhlman, P. D. Hustad in Imino- and amido-pyridinate d-Block Metal Complexes in Polymerization/Oligomerization Catalysis, Vol.35-Catalysis by Metal Complexes series (Eds.: G. Giambastiani, J. Cámpora), Springer, London, 2011, pp.197-281.
2. D. J. Arriola, E. M. Carnahan, P. D. Hustad, R. L. Kuhlman, T. T. Wenzel, Science 2006, 312, 714-719.
3. C. Zuccaccia, A. Macchioni, V. Busico, R. Cipullo, G. Talarico, F. Alfano, H. W. Boone, K. A. Frazier, P. D. Hustad, J. C. Stevens, P. C. Vosejpka, K. A. Abboud, J. Am. Chem. Soc. 2008, 130, 10354-10368.
4. C. Zuccaccia, V. Busico, R. Cipullo, G. Talarico, R. D. J. Froese, P. C. Vosejpka, P. D. Hustad, A. Macchioni, Organometallics 2009, 28, 5445-5458.
5. L. Luconi, G. Giambastiani, A. Rossin, C. Bianchini, A. Lledós, Inorg. Chem. 2010, 49, 6811-6813.
6. L. Luconi, A. Rossin, G. Tuci, I. Tritto, L. Boggioni, J. J. Klosin, C. N. Theriault, G. Giambastiani, Chem. Eur. J. 2012, 18, 671-687.
7. For general and more specialized reviews on hydroamination and its asymmetric version:.
8. K. D. Hesp, M. Stradiotto, ChemCatChem 2010, 2, 1192.
9. G. Zi, Dalton Trans. 2009, 9101.
10. S. C. Chemler, Org. Biomol. Chem. 2009, 7, 3009.
11. T. E. Müller, K. C. Hultzsch, M. Yus, F. Foubelo, M. Tada, Chem. Rev. 2008, 108, 3795.
12. I. Aillaud, J. Collin, J. Hannedouche, E. Schulz, Dalton Trans. 2007, 5105.
13. R. Severin, S. Doye, Chem. Soc. Rev. 2007, 36, 1407.
14. K. C. Hultzsch, Adv. Synth. Catal. 2005, 347, 367.
15. K. C. Hultzsch, Org. Biomol. Chem. 2005, 3, 1819.
16. S. Hong, T. J. Marks, Acc. Chem. Res. 2004, 37, 673.
17. P. W. Roesky, T. E. Müller, Angew. Chem. 2003, 115, 2812; Angew. Chem. Int. Ed. 2003, 42, 2708.
18. T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675.
19. For a selection of early and more recent reports on alkali-metal-catalyzed inter- and intramolecular hydroamination on unactivated alkenes, see:.
20. B. W. Howk, E. L. Little, S. L. Scott, G. M. Whitman, J. Am. Chem. Soc. 1954, 76, 1899.
21. R. Stroh, J. Ebersberger, H. Haberland, W. Hahn, Angew. Chem. 1957, 69, 124.
22. B. E. Evans, P. S. Anderson, M. E. Christy, C. D. Colton, D. C. Remy, K. E. Rittle, E. L. Engelhardt, J. Org. Chem. 1979, 44, 3127.
23. V. Khedkar, A. Tillack, C. Benisch, J.-P. Melder, M. Beller, J. Mol. Catal. A-Chem. 2005, 241, 175.
24. H. Fujita, M. Tokuda, M. Nitta, H. Suginome, Tetrahedron Lett. 1992, 33, 6359.
25. A. Ates, C. Quinet, Eur. J. Org. Chem. 2003, 1623.
26. C. Quinet, L. Sampoux, I. E. Markó, Eur. J. Org. Chem. 2009, 1806. For enantioselective lithium-catalyzed hydroamination, see:.
27. P. H. Martinez, K. C. Hultzsch, F. Hampel, Chem. Commun. 2006, 2221.
28. T. Ogata, A. Ujhara, S. Tsuchida, T. Shimizu, A. Kaneshige, K. Tomioka, Tetrahedron Lett. 2007, 48, 6648.
29. J. Deschamp, C. Olier, E. Schulz, R. Guillot, J. Hannedouche, J. Collin, Adv. Synth. Catal. 2010, 352, 2171.
30. J. Deschamp, J. Collin, J. Hannedouche, E. Schulz, Eur. J. Org. Chem. 2011, 3329.
31. For seminal work in this field, see:.
32. M. R. Gagné, T. J. Marks, J. Am. Chem. Soc. 1989, 111, 4108.
33. M. R. Gagné, S. P. Nolan, T. J. Marks, Organometallics 1990, 9, 1716.
34. M. R. Gagné, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 275.
35. M. R. Gagné, L. Brard, V. P. Conticello, M. A. Giardello, C. L. Stern, T. J. Marks, Organometallics 1992, 11, 2003. For a selection of rare-earth catalyzed (enantioselective) intra- and intermolecular hydroamination reaction, see:.
36. Y. Li, T. J. Marks, Organometallics 1996, 15, 3770.
37. J. S. Ryu, G. Y. Li, T. J. Marks, J. Am. Chem. Soc. 2003, 125, 12584.
38. S. Hong, S. Tian, M. V. Metz, T. J. Marks, J. Am. Chem. Soc. 2003, 125, 14768.
39. P. N. O'Shaughnessy, P. D. Knight, C. Morton, K. M. Gillespie, P. Scott, Chem. Commun. 2003, 1770.
40. J. Y. Kim, T. Livinghouse, Org. Lett. 2005, 7, 1737.
41. N. Meyer, A. Zulys, P. W. Roesky, Organometallics 2006, 25, 4179.
42. D. V. Gribkov, K. C. Hultzsch, F. Hampel, J. Am. Chem. Soc. 2006, 128, 3748.
43. I. Aillaud, J. Collin, C. Duhayon, R. Guillot, D. Lyubov, E. Schulz, A. Trifonov, Chem. Eur. J. 2008, 14, 2189.
44. G. Zi, L. Xiang, H. Song, Organometallics 2008, 27, 1242.
45. Y. Chapurina, J. Hannedouche, J. Collin, R. Guillot, E. Schulz, A. Trifonov, Chem. Commun. 2010, 46, 6918.
46. A. L. Reznichenko, H. N. Nguyen, K. C. Hultzsch, Angew. Chem. 2010, 122, 9168; Angew. Chem. Int. Ed. 2010, 49, 8984.
47. Y. Chapurina, H. Ibrahim, R. Guillot, E. Kolodziej, J. Collin, A. Trifonov, E. Schulz, J. Hannedouche, J. Org. Chem. 2011, 76, 10163.
48. D. V. Vitanova, F. Hampel, K. C. Hultzsch, J. Organomet. Chem. 2011, 696, 321.
49. P. Benndorf, J. Jenter, L. Zielke, P. W. Roesky, Chem. Commun. 2011, 47, 2574.
50. H. M. Lovick, D. K. An, T. S. Livinghouse, Dalton Trans. 2011, 40, 7697.
51. For a selection of late transition metal-catalyzed hydroamination, see:.
52. R. Dorta, P. Egli, F. Zurcher, A. Togni, J. Am. Chem. Soc. 1997, 119, 10857.
53. M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 9546.
54. O. Löber, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2001, 123, 4366.
55. M. Utsunomiya, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 14286.
56. C. F. Bender, R. A. Widenhoefer, J. Am. Chem. Soc. 2005, 127, 1070.
57. R. L. LaLonde, B. D. Sherry, E. J. Kang, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 2452.
58. G. L. Hamilton, E. J. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496.
59. Z. Zhang, C. F. Bender, R. A. Widenhoefer, J. Am. Chem. Soc. 2007, 129, 14148.
60. J. S. Zhou, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 12220.
61. Z. Liu, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 1570.
62. C. F. Bender, W. B. Hudson, R. A. Widenhoefer, Organometallics 2008, 27, 2356.
63. M. Ohmiya, T. Moriya, M. Sawamura, Org. Lett. 2009, 11, 2145.
64. Z. Zhang, S. D. Lee, R. A. Widenhoefer, J. Am. Chem. Soc. 2009, 131, 5372.
65. K. D. Hesp, S. Tobisch, M. Stradiotto, J. Am. Chem. Soc. 2010, 132, 413.
66. X. Shen, S. L. Buchwald, Angew. Chem. 2010, 122, 574; Angew. Chem. Int. Ed. 2010, 49, 564.
67. Z. Liu, H. Yamamichi, S. Madrahimov, J. F. Hartwig, J. Am. Chem. Soc. 2011, 133, 2772.
68. O. Kanno, W. Kuriyama, Z. Wang, J. F. D. Toste, Angew. Chem. 2011, 123, 10093; Angew. Chem. Int. Ed. 2011, 50, 9919.
69. For cationic groupIV metal-catalyzed hydroamination of aminoalkenes, see:.
70. P. D. Knight, I. Munslow, P. N. O'Shaughnessy, P. Scott, Chem. Commun. 2004, 894.
71. D. V. Gribkov, K. C. Hultzsch, Angew. Chem. 2004, 116, 5659; Angew. Chem. Int. Ed. 2004, 43, 5542.
72. X. Wang, Z. Chen, X.-L. Sun, Y. Tang, Z. Xie, Org. Lett. 2011, 13, 4758.
73. A. Mukherjee, S. Nembenna, T. K. Sen, S. PillaiSarish, P. Kr. Ghorai, H. Ott, D. Stalke, S. K. Mandal, H. W. Roesky, Angew. Chem. 2011, 123, 4054; Angew. Chem. Int. Ed. 2011, 50, 3968.
74. For neutral groupIV metal-catalyzed hydroamination of aminoalkenes, see:.
75. R. K. Thomson, J. A. Bexrud, L. L. Schafer, Organometallics 2006, 25, 4069.
76. M. C. Wood, D. C. Leitch, C. S. Yeung, J. A. Kozak, L. L. Schafer, Angew. Chem. 2006, 119, 358; Angew. Chem. Int. Ed. 2006, 46, 354.
77. S. Majumder, A. L. Odom, Organometallics 2008, 27, 1174.
78. A. L. Gott, A. J. Clarke, G. J. Clarkson, P. Scott, Chem. Commun. 2008, 1422.
79. C. Müller, W. Saak, S. Doye, Eur. J. Org. Chem. 2008, 2731.
80. J. Cho, T. K. Hollis, T. R. Helgert, E. J. Valente, Chem. Commun. 2008, 5001.
81. D. C. Leitch, P. R. Payne, C. R. Dunbar, L. L. Schafer, J. Am. Chem. Soc. 2009, 131, 18246.
82. A. L. Reznichenko, K. C. Hultzsch, Organometallics 2010, 29, 24.
83. J. A. Bexrud, L. L. Schafer, Dalton Trans. 2010, 39, 361.
84. Y.-C. Hu, C.-F. Liang, J.-H. Tsai, G. P. A. Yap, Y.-T. Chang, T.-G. Ong, Organometallics 2010, 29, 3357.
85. J. Cho, T. K. Hollis, E. J. Valente, J. M. Trate, J. Organomet. Chem. 2011, 696, 373.
86. R. O. Ayinla, L. L. Schafer, Dalton Trans. 2011, 40, 7769.
87. H. Kim, P. H. Lee, T. Livinghouse, Chem. Commun. 2005, 5205.
88. J. A. Bexrud, J. D. Beard, D. C. Leitch, L. L. Schafer, Org. Lett. 2005, 7, 1959.
89. H. Kim, Y. K. Kim, J. H. Shim, M. Kim, M. Han, T. Livinghouse, P. H. Lee, Adv. Synth. Catal. 2006, 348, 2609.
90. D. A. Watson, M. Chiu, R. G. Bergman, Organometallics 2006, 25, 4731.
91. A. L. Gott, A. J. Clarke, G. J. Clarkson, P. Scott, Organometallics 2007, 26, 1729.
92. L. Xiang, H. Song, G. Zi, Eur. J. Inorg. Chem. 2008, 1135.
93. G. Zi, Q. Wang, L. Xiang, H. Song, Dalton Trans. 2008, 5930.
94. G. Zi, X. Liu, L. Xiang, H. Song, Organometallics 2009, 28, 1127.
95. G. Zi, F. Zhang, L. Xue, L. Ai, H. Song, J. Organomet. Chem. 2010, 695, 730.
96. G. Zi, F. Zhang, L. Xiang, Y. Chen, W. Fang, H. Song, Dalton Trans. 2010, 39, 4048.
97. B. D. Stubbert, T. J. Marks, J. Am. Chem. Soc. 2007, 129, 6149.
98. see also Refs.[9c, d].
99. For zwitterionic groupIV metal-catalyzed hydroamination of aminoalkenes, see:.
100. K. Manna, A. Ellern, A. D. Sadow, Chem. Commun. 2010, 46, 339.
101. K. Manna, S. Xu, A. D. Sadow, Angew. Chem. 2011, 123, 1905-1908; Angew. Chem. Int. Ed. 2011, 50, 1865-1868.
102. For significant contributions on groupII- and V-based catalysts for hydroamination:.
103. X. Zhang, T. J. Emge, K. C. Hultzsch, Angew. Chem. 2012, 124, 406; Angew. Chem. Int. Ed. 2012, 51, 394.
104. S. R. Neal, A. Ellern, A. D. Sadow, J. Organomet. Chem. 2011, 696, 228.
105. J. S. Wixey, B. D. Ward, Chem. Commun. 2011, 47, 5449.
106. J. S. Wixey, B. D. Ward, Dalton Trans. 2011, 40, 7693.
107. P. Horrillo-Martínez, K. C. Hultzsch, Tetrahedron Lett. 2009, 50, 2054.
108. F. Buch, S. Harder, Z. Naturforsch. B 2008, 63, 169.
109. B. Liu, T. Roisnel, J.-F. Carpentier, Y. Sarazin, Angew. Chem. 2012, 124, 5027; Angew. Chem. Int. Ed. 2012, 51, 4943.
110. A. L. Reznichenko, T. J. Emge, S. Audörsch, E. G. Klauber, K. C. Hultzsch, B. Schmidt, Organometallics 2011, 30, 921.
111. K. E. Near, B. M. Chapin, D. C. McAnnally-Linz, A. R. Johnson, J. Organomet. Chem. 2011, 696, 81.
112. M. C. Hansen, C. A. Heusser, T. C. Narayan, K. E. Fong, N. Hara, A. W. Kohn, A. R. Venning, A. L. Rheingold, A. R. Johnson, Organometallics 2011, 30, 4616.
113. F. Zhang, H. Song, G. Zi, Dalton Trans. 2011, 40, 1547.
114. L. Luconi, D. M. Lyubov, C. Bianchini, A. Rossin, C. Faggi, G. K. Fukin, A. V. Cherkasov, A. S. Shavyrin, A. A. Trifonov, G. Giambastiani, Eur. J. Inorg. Chem. 2010, 608-620 and references therein.
115. R. D. J. Froese, P. D. Hustad, R. L. Kuhlman, T. T. Wenzel, J. Am. Chem. Soc. 2007, 129, 7831-7840.
116. K. A. Frazier, H. W. Boone, P. C. Vosejpka, J. C. Stevens, (DOW Global Techologies Inc.), U.S. Pat. Appl. Publ. No. US 2004/0220050A1.
117. G. J. Domski, J. B. Edson, I. Keresztes, E. B. Lobkovsky, G. W. Coates, Chem. Commun. 2008, 6137-6139.
118. G. J. Domski, E. B. Lobkovsky, G. W. Coates, Macromolecules 2007, 40, 3510-3513.
119. 4 in a catalytic amount.
120. Although deeper investigations and kinetic studies are needed, this rate similarity for the formation of a five- and six-membered ring seems to be against the general trend for classical stereoelectronically controlled cyclization processes. This observation was previously noted in the field of groupIV metal catalyzed hydroamination of aminoalkenes, see Ref.[9a] for an example.
121. For a selection of groupIV metal-catalyzed hydroaminoalkylation, see;.
122. W. A. Nugent, D. W. Ovenall, S. J. Holmes, Organometallics 1983, 2, 161.
123. P. W. Roesky, Angew. Chem. 2009, 121, 4988; Angew. Chem. Int. Ed. 2009, 48, 4892.
124. J. A. Bexrud, P. Eisenberger, D. C. Leitch, P. R. Payne, L. L. Schafer, J. Am. Chem. Soc. 2009, 131, 2116.
125. R. Kubiak, I. Prochnow, S. Doye, Angew. Chem. 2009, 121, 1173; Angew. Chem. Int. Ed. 2009, 48, 1153.
126. R. Kubiak, I. Prochnow, S. Doye, Angew. Chem. 2010, 122, 2683; Angew. Chem. Int. Ed. 2010, 49, 2626.
127. For an example of hydroamination side reactivity by using groupIV metal complexes, see Ref.[10f].
128. Ph, Zr, see Ref.[4].
129. [4b] and in this case it is reasonably caused by the combination of three factors: 1)disorder present on the dimethylamido ligands; 2)the (very) low temperature data collection, and 3)the employ of two-dimensional CCD X-ray detectors.
130. Ph, Zr) its isolation in crystals for X-ray diffraction analysis required severe and controlled conditions.
131. IV-amido catalysts on the model hydroamination/cyclization reaction of 1, see Refs.[10b, c, g, k, l, m].
132. Th, Zr, in toluene at 100°C was found to be 25:75mol%.
133. A zero-order dependence of the hydroamination reaction rate on aminoalkene concentration was also observed with some groupIV metal based catalytic systems, see Refs.[10e, x].
134. For rare exceptions of neutral groupIV catalyzed hydroamination of secondary aminoalkenes, see Refs.[10h, kx].
135. CrysAlisCCD 1.171.31.2 (release 07-07-2006), CrysAlis171.NET, Oxford Diffraction Ltd.
136. CrysAlis RED 1.171.31.2 (release 07-07-2006), CrysAlis171.NET, Oxford Diffraction Ltd.
137. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115-119.
138. G.M. Sheldrick, SHELXL, 1997.
139. L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.