Platinum-catalyzed intermolecular hydroamination of alkenes: Halide-anion-promoted catalysis

European Journal of Inorganic Chemistry

Volumn , Issue 30, 2007, Pages 4711-4722

  Brunet, Jean Jacques ^a   Chu, Ngoc Chau ^a   Rodriguez Zubiri, Mireia ^a  

^a LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

Alkenes; Homogeneous catalysis; Intermolecular hydroamination; Ionic liquids; Platinum

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; ETHYLENE; PLATINUM;

1-HEXENE; AEROBIC CONDITION; ANIONIC MOIETIES; CO CATALYSTS; HALIDE ANIONS; HOMOGENEOUS CATALYSIS; HYDROAMINATIONS; INTERMOLECULAR HYDROAMINATION; PROMOTING EFFECT;

IONIC LIQUIDS;

EID: 35848961637     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200700737     Document Type: Short Survey

References (125)

1. M. Turcotte, K. S. Hayes in Kirk-Othmer Encyclopedia of Chemistry and Technology, Wiley & Sons, New York, 2001, vol. 2, pp. 537-553.
2. K. Visek in Kirk-Othmer Encyclopedia of Chemistry and Technology, Wiley & Sons, New York, 2003, vol. 2, pp. 518-537.
3. P. J. Chenier in Survey of Industrial Chemistry, 2nd ed., VCH, Weinheim, 1992.
4. K. Weissermel, H.-J. Harpe in Industrial Organic Chemistry, 2nd ed., VCH, Weinheim, 1993.
5. V. Grignard in Traité de Chimie Organique, Masson & Cie, Paris, 1935, vol. 12.
6. J. March in Advanced Organic Chemistry, 4th ed., Wiley & Sons, New York, 1992.
7. P. Sabatier, A. Mailhe, Compt. Rend. Sc. Heb. Acad. Sci. 1909, 148, 898.
8. A. Baiker, J. Kijenski, Catal. Rev. Sci. Eng. 1985, 27, 653-697.
9. S. A. Lawrence in Amines, Cambridge University Press, Cambridge, 2004.
10. J. Falbe in New Syntheses with Carbon Monoxide, Springer Verlag, Berlin, 1980.
11. F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079-3159.
12. Tetrahedron Report 144,
13. M. B. Gasc, A. Lattes, J. J. Perié, Tetrahedron 1983, 39, 703-731.
14. D. Steinborn, R. Taube, Z. Chem. 1986, 349-359.
15. J. J. Brunet, D. Neibecker, F. Niedercorn, J. Mol. Catal. 1989, 49, 235-259.
16. D. M. Roundhill, Chem. Rev. 1992, 92, 1-27.
17. R. Taube in Applied Homogeneous Catalysis with Organometallic Complexes (Eds.: B. Cornils, W. Herrmann), VCH, Weinheim, 1996, vol. 2, pp. 507-521.
18. D. M. Roundhill, Catal. Today 1997, 37, 155-165.
19. J. J. Brunet, Gazz. Chim. Ital. 1997, 127, 111-118.
20. a) T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675-703;
21. b) T. E. Müller, M. Beller in Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998, vol. 2, pp. 316-330;
22. c) M. Beller, J. Seyad, A. Tillack, H. Jiao, Angew. Chem. Int. Ed. 2004, 43, 3368-3398.
23. H. F. Koch, L. A. Girard, D. M. Roundhill, Polyhedron 1999, 18, 2275-2279.
24. a) J-J. Brunet, D. Neibecker in Catalytic Heterofunctionalization (Eds.: A. Togni, H. Grützmacher), VCH, Weinheim, 2001, pp. 91-141;
25. b) M. Beller, C. Breindl, M. Eichberger, C. Hartung, J. Seayad, O. R. Thiel, A. Tillack, H. Trauthwein, Synlett 2002, 10, 1579-1594.
26. P. W. Roesky, T. E. Müller, Angew. Chem. Int. Ed. 2003, 42, 2708-2710.
27. K. C. Hultzsch, Adv. Synth. Catal. 2005, 347, 367-391.
28. Transition metal catalysts: a) U. Nettekoven, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 1166-1167;
29. b) M. Utsunomiya, R. Kuwano, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 5608-5609;
30. c) M. Utsunomiya, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 14286-14287;
31. d) M. Utsunomiya, J. F. Hartwig, J. Am. Chem. Soc. 2004, 126, 2702-2703;
32. e) J. F. Hartwig, Pure Appl. Chem. 2004, 76, 507-516;
33. f) H. Qian, R. A. Widenhoefer, Org. Lett. 2005, 7, 2635-2638;
34. g) L. T. Kaspar, B. Fingerhut, L. Ackermann, Angew. Chem. Int. Ed. 2005, 44, 5972-5974;
35. h) O. Jimenez, T. E. Müller, C. Sievers, A. Spirkl, J. A. Lercher, Chem. Commun. 2006, 2974-2976.
36. Base catalysts: i) M. Beller, C. Breindl, Tetrahedron 1998, 54, 6359-6368;
37. j) M. Beller, C. Breindl, T. H. Riermeier, M. Eichberger, H. Trauthwein, Angew. Chem. Int. Ed. 1998, 37, 3389-3391;
38. k) J. Herwig, M. Beller, C. Breindl, WO 9936412, 1999;
39. l) D. Tzalis, C. Koradin, P. Knochel, Tetrahedron Lett. 1999, 40, 6193-6195.
40. a) J. Pawlas, Y. Nakao, M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 3669-3679;
41. b) C. Brouwer, C. He, Angew. Chem. Int. Ed. 2006, 45, 1744-1747;
42. c) A. M. Johns, M. Utsunomiya, C. D. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 1828-1839;
43. d) H. Qin, N. Yamagiwa, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 1611-1614.
44. For an external analysis of the work developed by Hartwig et al. on the hydroamination of vinylarenes, see: J. J. Brunet, R. Poli, Chemtracts: Inorg. Chem. 2004, 17, 381-387.
45. a) Y. K. Kim, T. Livinghouse, Y. Horino, J. Am. Chem. Soc. 2003, 125, 9560-9561;
46. b) J. Collin, J.-C. Daran, E. Schulz, A. Trifonov, Chem. Commun. 2003, 3048-3049:
47. c) K. C. Hultzsch, F. Hampel, T. Wagner, Organometallics 2004, 23, 2601-2612;
48. d) S. Hong, T. J. Marks, Acc. Chem. Res. 2004, 37, 673-686;
49. e) J. Y. Kim, T. Livinghouse, Org. Lett. 2005, 7, 4391-4393;
50. f) K. Komeyama, T. Morimoto, K. Takaki, Angew. Chem. Int. Ed. 2006, 45, 2938-2941;
51. g) X. Y. Liu, C. H. Li, C. M. Che, Org. Lett. 2006, 8, 2707-2710;
52. h) S. Bambirra, H. Tsurugi, D. van Leusen, B. Hessen, Dalton Trans. 2006, 1157-1161;
53. i) M. Rastätter, A. Zulys, P. W. Roesky, Chem. Commun. 2006, 874-876:
54. j) D. Riegert, J. Collin, A. Medour, E. Schultz, A. Trifonov, J. Org. Chem. 2006, 71, 2514-2517;
55. k) A. Takemiya, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 6042-6043;
56. l) C. Müller, C. Loos, N. Schulenberg, S. Doye, Eur. J. Org. Chem. 2006, 2499-2503;
57. m) D. A. Watson, M. Chiu, R. G. Bergman, Organometallics 2006, 25, 4731-4733;
58. n) J. Zhao, T. J. Marks, Organometallics 2006, 25, 4763-4772;
59. o) D. V. Gribkov, K. C. Hultzsch, F. Hampel, J. Am. Chem. Soc. 2006, 128, 3748-3759;
60. p) K. Khedkar, A. Tillack, C. Benisch, J. P. Melder, M. Beller, J. Mol. Catal. A 2005, 241, 175-183.
61. a) T. E. Daubert, R. P. Danner in Physical Thermodynamic Properties of Pure Chemicals: Data Compilation, Taylor & Francis, Washington, DC, 1993;
62. b) J. B. Pedley, R. D. Naylor, S. P. Kirby in Thermochemical Data of Organic Compounds, 2nd ed., Chapman and Hall, London, 1986, Appendix Table 1.2.
63. F. R. Hartley in Comprehensive Organometallic Chemistry, (Eds: G. Wilkinson, F. G. A Stone, E. W. Abel), Pergamon Press, 1982, vol 6, pp. 471-762.
64. a) A. Panunzi, R. Palumbo, A. De Renzi, G. Paiaro, Chim. Ind. (Milan) 1968, 50, 924-925;
65. b) A. Panunzi, A. De Renzi, R. Palumbo, G. Paiaro, J. Am. Chem. Soc. 1969, 91, 3879-3883;
66. c) A. Panunzi, A. De Renzi, G. Paiaro, J. Am. Chem. Soc. 1970, 92, 3488-3489;
67. d) E. Benedetti, A. De Renzi, G. Paiaro, A. Panunzi, C. Pedone, Gazz. Chim. Ital. 1972, 102, 744-754;
68. e) V. Romano, G. Paiaro, Chim. Ind. (Milan) 1972, 54, 658-659;
69. f) P. D. Kaplan, P. Schmidt, M. Orchin, J. Am. Chem. Soc. 1968, 90, 4175-4176.
70. D. Hollings, M. Green, D. V. Claridge, J. Organomet. Chem. 1973, 54, 399-402.
71. a) J. Ambühl, P. S. Pregosin, L. M. Venanzi, G. Ughetto, L. Zambonelli, Angew. Chem. Int. Ed. Engl. 1975, 14, 369;
72. b) J. Ambuehl, P. S. Pregosin, L. M. Venanzi, G. Ughetto, J. Organomet. Chem. 1978, 160, 329-335;
73. c) J. Ambuehl, P. S. Pregosin, L. M. Venanzi, G. Consiglio, F. Bachechi, L. Zambonelli, J. Organomet. Chem. 1979, 181, 255-269.
74. a) I. M. Al-Najjar, M. Green, S. J. Kerrison, R. J. Sadler, J. Chem. Soc. Chem. Commun. 1979, 311-312;
75. b) I. M. Al-Najjar, M. Green, J. Chem. Soc. Dalton Trans. 1979, 1651-1656;
76. c) M. Green, J. K. K. Sarhan, I. M. Al-Najjar, J. Chem. Soc. Dalton Trans. 1981, 1565-1571;
77. d) J. K. K. Sarhan, M. Green, I. M. Al-Najjar, J. Chem. Soc. Dalton Trans. 1984, 771-777.
78. [32] reported a platinum-promoted cyclization of aminoalkenes (e.g. 1-pentenylamine) that may appear catalytic in character. However, as noted by the authors, the reaction rates are so low that "its synthetic exploitation would not represent a significant improvement over existing stoichiometric processes".
79. J. J. Brunet, M. Cadena, N. C. Chu, O. Diallo, K. Jacob, E. Mothes, Organometallics 2004, 23, 1264-1268.
80. a) X. Wang, R. A. Widenhoefer, Organometallics 2004, 23, 1649-1651;
81. b) C. F. Bender, R. A. Widenhoefer, J. Am. Chem. Soc. 2005, 127, 1070-1071.
82. D. Karshtedt, A. T. Bell, T. D. Tilley, J. Am. Chem. Soc. 2005, 127, 12640-12646.
83. J. J. Brunet, D. Neibecker, K. Philippot, J. Chem. Soc. Chem. Commun. 1992, 1215-1216.
84. J. J. Brunet, G. Commenges, D. Neibecker, K. Philippot, J. Organomet. Chem. 1994, 469, 221-228.
85. J. J. Brunet, G. Commenges, D. Neibecker, K. Philippot, L. Rosenberg, Inorg. Chem. 1994, 33, 6373-6379.
86. J. J. Brunet, G. Commenges, D. Neibecker, L. Rosenberg, J. Organomet. Chem. 1996, 522, 117-122.
87. M. Badri, J. J. Brunet, R. Perron, Tetrahedron Lett. 1992, 33, 4435-4438.
88. a) T. Welton, Chem. Rev. 1999, 99, 2071-2083;
89. b) P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 2000, 39, 3772-3789;
90. c) R. Sheldon, Chem. Commun. 2001, 2399-2407.
91. H. Olivier-Bourbigou, L. Magna, J. Mol. Catal. A 2002, 182-183, 419-437.
92. J. Dupont, R. F. De Souza, P. A. Z. Suarez, Chem. Rev. 2002, 102, 3667-3692.
93. P. Wasserscheid, T. Welton (Eds.), Ionic Liquids in Synthesis, Wiley-VCH, Verlag GmbH & Co, Weinheim, 2002.
94. D. R. Coulson (E. I. du Pont de Nemours and Co.), US 3,758,586, 1973.
95. D. R. Coulson, Tetrahedron Lett. 1971, 12, 429-430.
96. H. M. Senn, P. E. Blöchl, A. Togni, J. Am. Chem. Soc. 2000, 122, 4098-4107.
97. J. J. Brunet, N. C. Chu, O. Diallo, E. Mothes, J. Mol. Catal. A 2003, 198, 107-110.
98. E. R. Perez, R. M. Carvalho, R. H. A. Santos, M. T. P. Gambardella, B. S. Lima-Neto, Polyhedron 2003, 22, 3289-3292.
99. a) S. E. Diamond, A. Szalkiewicz, F. Mares, J. Am. Chem. Soc. 1979, 101, 490-491;
100. b) S. E. Diamond, F. Mares (Allied Chemical Corp.). US 4,215,218, 1980.
101. J. J. Brunet, M. Cadena, N. C. Chu, O. Diallo, K. Jacob, E. Mothes, Organometallies 2004, 23, 1264-1268.
102. a) G. Pez, J. E. Galles, Pure Appl. Chem. 1985, 57, 1917-1926;
103. b) G. Pez (Allied Chemical Corp.), US 4.302,603, 1981.
104. S. E. Diamond, A. Szalkiewicz, F. Mares, Fund. Res. Homogeneous Catal. 1979, 3, 345-358.
105. F. Y. Kwong, A. Klapars, S. L. Buchwald, Org. Lett. 2002, 4, 581-584.
106. M. Novotny, R. Kump, F. Merli, L. J. Todd, Anal. Chem. 1980, 52, 401-406.
107. J. J. Brunet, N. C. Chu, O. Diallo, Organometallics 2005, 24, 3104-3110.
108. S. T. Handy, M. Okello, Tetrahedron Lett. 2003, 44, 8395-8397, and references herein.
109. T. Jeffery, Tetrahedron 1996, 52, 10113-10130.
110. C. Amatore, A. Jutand, J. Organomet. Chem. 1999, 576, 254-278.
111. P. M. Maitlis, A. Haynes, B. R. James, M. Catellani, G. P. Chiusoli, Dalton Trans. 2004, 3409-3419.
112. R. G. Denning, L. M. Venanzi, J. Chem. Soc. A 1967, 328-337.
113. a) A. C. Cope, C. R. Ganellin, H. W. Johnson, T. V. Van Auken, H. J. S. Winkler, J. Am. Chem. Soc. 1963, 85, 3276-3279;
114. b) S. Hupp, G. Dahlgreen, Inorg. Chem. 1976, 15, 2349-2353.
115. S. Anguille, J. J. Brunet, N. C. Chu, O. Diallo, C. Pages, S. Vincendeau, Organometallic 2006, 25, 2943-2948.
116. a) S. I. Murahashi, N. Yoshimura, T. Tsumiyama, T. Kojima, J. Am. Chem. Soc. 1983, 105, 5002-5011;
117. b) S. I. Murahashi, Angew. Chem. Int. Ed. Engl. 1995, 34, 2443-2465.
118. a) C. S. Cho, B. H. Oh, T. J. Kim, S. C. Shim, Chem. Commun. 2000, 1885-1888;
119. b) C. S. Cho, J. S. Kim, T. J. Oh, S. C. Shim, N. S. Yoon, Tetrahedron 2000, 56, 7747-7750;
120. c) C. S. Cho, T. K. Kim, B. T. Kim, T. J. Kim, S. C. Shim, J. Organomet. Chem. 2002, 650, 65-68.
121. M. Rodriguez-Zubiri, J. J. Brunet, S. Anguille, J. Mol. Catal. A 2007, 271, 146-151.
122. See, for example: a) X. Wang, S. M. Lu, P. Y. Yang, X. W. Han, Y. G. Zhou, J. Am. Chem. Soc. 2003, 125, 10536-10537;
123. b) D. Xiao, X. Zhang, Angew. Chem. Int. Ed. 2001, 40, 3425-3428.
124. D. Konya, K. Q. Almeida Leñero, E. Drent, Organometallics 2006, 25, 3166-3174.
125. 4] have recently been reported to exhibit similar catalytic activities for the cycloisomerization of polyunsaturated precursors: J. Marco-Contelles, N. Arroyo, S. Anjum, E. Mainetti, N. Marion, K. Cariou, G. Lemière, V. Mouriès, L. Fensterbank, M. Malacria, Eur. J. Org. Chem. 2006, 4618-4633.