Advances and adventures in amination reactions of olefins and alkynes

Synlett

Volumn , Issue 10, 2002, Pages 1579-1594

  Beller, Matthias ^a   Breindl, Claudia ^a   Eichberger, Martin ^a   Hartung, Christian G ^a   Seayad, Jayasree ^a   Thiel, Oliver R ^a   Tillack, Annegret ^a   Trauthwein, Harald ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Alkynes; Aminations; Amines; Homogeneous catalysis; Olefins

Indexed keywords

2 VINYLPYRIDINE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; ANILINE DERIVATIVE; AROMATIC COMPOUND; NORBORNADIENE DERIVATIVE; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; RHODIUM; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; HYDROGENATION; ISOMERISM; MOLECULAR MECHANICS; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0036399736     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34240     Document Type: Article

References (122)

1. (a) March, J. Advanced Organic Chemistry, 4th Ed.; Wiley: New York, 1992, 768; and references therein.
2. (b) Collman, J. P.; Trost, B. M.; Veroeven, T. R. In Comprehensive Organometallic Chemistry, Vol. 8; Wilkinson, G.; Stone, F. G. A., Eds.; Pergamon Press: Oxford, 1982, 892; and references therein.
3. (c) Gibson, M. S. In The Chemistry of Amino Group; Patai, S., Ed.; Interscience: New York, 1968, 61.
4. (a) Hartwig, J. F. Synlett 1997, 329.
5. (b) Roundhill, D. M. Chem. Rev. 1992, 92, 1.
6. (a) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675.
7. (b) Müller, T. E.; Beller, M. In Transition Metals for Organic Synthesis, Vol. 2; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998, 316.
8. (c) Haak, E.; Doye, S. Chem. Unserer Zeit 1999, 33, 296.
9. (d) Brunet, J. J.; Neibecker, D.; Niedercorn, F. J. Mol. Catal. 1989, 49, 235.
10. Steinborn, D.; Taube, R. Z. Chem. 1986, 26, 349.
11. Taube, R. In Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 1; Cornils, B.; Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 1998, 507.
12. (a) Bozel, J. J.; Hegedus, L. S. J. Org. Chem. 1981, 46, 2561.
13. (b) Suminov, S. I.; Kost, A. N. Russ. Chem. Rev. 1969, 38, 884.
14. (c) Larock, R. C.; Leong, W. W. Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxord, 1991, 269.
15. (d) Jung, M. E. Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxord, 1991, 1.
16. (a) Howk, B. W.; Little, E. L.; Scott, S. L.; Whitman, G. M. J. Am. Chem. Soc. 1954, 76, 1899.
17. (b) Wollensak, J.; Closson, R. D. Org. Synth. 1963, 43, 45.
18. (c) Pez, G. P.; Galle, J. E. Pure. Appl. Chem. 1985, 57, 1917.
19. (d) Steinborn, D.; Thies, B.; Wagner, I.; Taube, R. Z. Chem. 1989, 29, 333.
20. (e) Beller, M.; Breindl, C. Tetrahedron 1998, 54, 6359.
21. (f) Beller, M.; Breindl, C.; Riermeier, T. H.; Eichberger, M.; Trauthwein, H. Angew. Chem. Int. Ed. 1998, 37, 3389; Angew. Chem. 1998, 110, 3571.
22. Beller, M.; Breindl, C.; Riermeier, T. H.; Eichberger, M.; Trauthwein, H. Angew. Chem. Int. Ed. 1998, 37, 3389; Angew. Chem. 1998, 110, 3571.
23. (g) Hartung, C. G.; Breindl, C.; Tillack, A.; Beller, M. Tetrahedron 2000, 56, 5175.
24. (h) Beller, M.; Breindl, C. Chemosphere 2001, 43, 21.
25. (a) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485.
26. (b) McGrane, P. L.; Livinghouse, T. J. Org. Chem. 1992, 57, 1323.
27. (c) McGrane, P. L.; Jensen, M.; Livinghouse, T. J. Am. Chem. Soc. 1992, 114, 5459.
28. (d) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708.
29. (e) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753.
30. (a) Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem. Int. Ed. 1999, 38, 3389; Angew. Chem. 1999, 111: 3584.
31. Haak, E.; Bytschkov, I.; Doye, S. Angew. Chem. Int. Ed. 1999, 38, 3389; Angew. Chem. 1999, 111: 3584.
32. (b) Haak, E.; Siebeneicher, H.; Doye, S. Org. Lett. 2000, 2, 1935.
33. (a) Brunet, J. J. Gazz. Chim. Ital. 1997, 127, 111.
34. (b) Beller, M.; Eichberger, M.; Trauthwein, H. In Catalysis of Organic Reactions; Herkes, F. E., Ed.; Marcel Dekker Inc.: New York, 1998, 319.
35. (c) Schaffrath, H.; Keim, W. J. Mol. Catal. A: Chem. 2001, 168, 9.
36. (a) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 1757.
37. (b) Eisen, M. S.; Straub, T.; Haskel, A. J. Alloys. Compd. 1998, 271, 116.
38. (c) Haskel, A.; Straub, T.; Eisen, M. S. Organometallics 1996, 15, 3773.
39. (d) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295.
40. (e) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707.
41. (f) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770.
42. (g) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994, 682.
43. (h) Giardell, M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241.
44. (i) Giardell, M. A.; Conticello, V. P.; Brard, L.; Sabat, M.; Rheingold, A. L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10212.
45. (j) Li, Y.; Fu, P. F.; Marks, T. J. Organometallics 1994, 13, 439.
46. (k) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275.
47. (l) Gagné, M. R.; Stern, C. L.; Gagné, M. R.; Nolan, S. P.; Marks, T. J. Organometallics 1990, 9, 1716.
48. (m) Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108.
49. (a) Hegedus, L. S.; Akermark, B.; Zetterberg, K.; Olsson, L. F. J. Am. Chem. Soc. 1984, 106, 7122.
50. (b) Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113; Angew. Chem. 1988, 100, 1147.
51. Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113; Angew. Chem. 1988, 100, 1147.
52. (c) Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, Vol. 74; University Sciences Books: Mill Valley, 1987, 409.
53. (d) Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, Vol 17; University Sciences Books: Mill Valley, 1987, 825.
54. (e) Eisenstein, O.; Hoffmann, R. J. Am. Chem. Soc. 1981, 103, 4308.
55. (f) Selington, A. L.; Trogler, W. C. Organometallics 1993, 12, 744.
56. Hegedus, L. S. Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, 551.
57. (a) Selington, A. L.; Cowan, R. L.; Trogler, W. C. Inorg. Chem. 1991, 30, 3371.
58. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 4206.
59. (c) Fryzuk, M. D.; Montgomery, C. D. Coord. Chem. Rev. 1989, 95, 1.
60. Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. Inorg. Chem. 1987, 26, 971.
61. Schulz, M.; Milstein, D. J. Chem. Soc., Chem. Commun. 1993, 318.
62. (a) Cowan, R. L.; Trogler, W. C. J. Am. Chem. Soc. 1989, 111, 4750.
63. (b) Diversi, P.; Ermini, L.; Ingrosso, G.; Lucherni, A.; Pinzino, C.; Sagramora, L. J. Organomet. Chem. 1995, 494, C1.
64. (a) Stern, E. W.; Spector, M. L. Proc. Chem. Soc. London 1961, 370.
65. (b) Akermark, B.; Bäckvall, J. E.; Hegedus, L. S.; Zetterberg, K.; Siirala-Hansén, K.; Sjöberg, K. J. Organomet. Chem. 1974, 72, 127.
66. (c) Panunzi, A.; De Renzi, A.; Paiaro, G. J. Am. Chem. Soc. 1970, 92, 3488.
67. (d) Hirai, H.; Sawai, H.; Makishima, S. Bull. Chem. Soc. Jpn. 1970, 43, 1148.
68. (a) Tsuji, J. Palladium Reagents and Catalysts Innovations in Organic Synthesis; Wiley & Sons: Chichester, 1995.
69. (b) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985.
70. (a) Hegedus, L. S.; Allen, G. F.; Waterman, E. L. J. Am. Chem. Soc. 1976, 98, 2674.
71. (b) Hegedus, L. S.; Allen, G. F.; Bozell, J. J.; Waterman, E. L. J. Am. Chem. Soc. 1978, 100, 5800.
72. Hegedus, L. S.; McKearin, J. M. J. Am. Chem. Soc. 1982, 104, 2444.
73. Larock, R. C.; Hightower, T. R.; Hasvold, L. A.; Peterson, K. P. J. Org. Chem. 1996, 61, 3584.
74. Hosokawa, T.; Takano, M.; Kuroki, Y.; Murahashi, S. Tetrahedron Lett. 1992, 33, 6643.
75. Brunet, J. J.; Neibecker, D.; Philippot, K. Tetrahedron Lett. 1994, 34, 3877.
76. Campi, E. M.; Jackson, W. R. J. Organomet. Chem. 1996, 523, 205.
77. Utimoto, K. Pure Appl. Chem. 1983, 55, 1845.
78. Fukuda, Y.; Utimoto, K.; Nozaki, H. Heterocycles 1987, 25, 297.
79. Lathbury, D.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1986, 114.
80. (a) Müller, T. E.; Pleier, A.-K. J. Chem. Soc. Dalton. Trans. 1999, 583.
81. (b) Müller, T. E.; Grosche, M.; Herdtweck, E.; Pleier, A.-K.; Walter, E.; Yan, Y. K. Organometallics 2000, 19, 170.
82. Burling, S.; Field, L. D.; Messerle, B. A. Organometallics 2000, 19, 87.
83. Kondo, T.; Okada, T.; Suzuki, T.; Mitsudo, T. J. Organomet. Chem. 2001, 622, 149.
84. (a) Ambüehl, J.; Pregosin, P. S.; Venanzi, L. M.; Ugetto, G.; Zambonelli, L. Angew. Chem., Int. Ed. Engl. 1975, 14, 369; Angew. Chem. 1975, 87, 380.
85. (a) Ambüehl, J.; Pregosin, P. S.; Venanzi, L. M.; Ugetto, G.; Zambonelli, L. Angew. Chem., Int. Ed. Engl. 1975, 14, 369; Angew. Chem. 1975, 87, 380.
86. (b) Ambüehl, J.; Pregosin, P. S.; Venanzi, L. M.; Consiglio, G.; Bachechi, F.; Zambonelli, L. J. Organomet. Chem. 1979, 181, 255.
87. Vogels, C. M.; Hayes, P. G.; Shaver, M.; Westcott, S. A. Chem. Commun. 2000, 51.
88. (a) Barluenga, J.; Aznar, F. Synthesis 1975, 704.
89. (b) Barluenga, J.; Aznar, F. Synthesis 1977, 195.
90. Barluenga, J.; Aznar, F. J. Chem. Soc. Perkin Trans. 1 1980, 2732.
91. Kadota, I.; Shibuya, A.; Lutete, L. M.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4570.
92. Tokunaga, M.; Eckert, M.; Wakatsuki, Y. Angew. Chem. Int. Ed. 1999, 38, 3222; Angew. Chem. 1999, 111, 3417.
93. Tokunaga, M.; Eckert, M.; Wakatsuki, Y. Angew. Chem. Int. Ed. 1999, 38, 3222; Angew. Chem. 1999, 111, 3417.
94. Uchimaru, Y. Chem. Commun. 1999, 1133.
95. Al-Masum, M.; Meguro, M.; Yamamoto, Y. Tetrahedron Lett. 1997, 38, 6071.
96. Coulson, D. R. Tetrahedron Lett. 1971, 12, 429.
97. Brunet, J. J.; Commenges, G.; Neibecker, D.; Philippot, K. J. Organomet. Chem. 1994, 469, 221.
98. Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem, Soc. 1988, 110, 6738.
99. Dorta, R.; Egli, P.; Zürcher, F.; Togni, A. J. Am. Chem. Soc. 1997, 119, 10857.
100. Togni, A.; Bieler, N.; Burckhardt, U.; Köllner, C.; Pioda, G.; Schneider, R.; Schnyder, A. Pure Appl. Chem. 1999, 71, 1531.
101. Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 9546.
102. Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366.
103. Kawatsura, M.; Hartwig, J. F. Organometallics 2001, 20, 1960.
104. Beller, M.; Eichberger, M.; Trauthwein, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 2225; Angew. Chem. 1997, 109, 2306.
105. Beller, M.; Eichberger, M.; Trauthwein, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 2225; Angew. Chem. 1997, 109, 2306.
106. Beller, M.; Trauthwein, H.; Eichberger, M.; Breindl, C.; Müller, T. E.; Zapf, A. J. Organomet. Chem. 1998, 566, 277.
107. Beller, M.; Trauthwein, H.; Eichberger, M.; Breindl, C.; Herwig, J.; Müller, T. E.; Thiel, O. R. Chem.-Eur. J. 1999, 5, 1306.
108. Senn, H. M.; Blöchl, P. E.; Togni, A. J. Am. Chem. Soc. 2000, 122, 4098.
109. Tillack, A.; Trauthwein, H.; Hartung, C. G.; Eichberger, M.; Pitter, S.; Jansen, A.; Beller, M. Monatsh. Chem. 2000, 131, 1327.
110. Beller, M.; Trauthwein, H.; Eichberger, M.; Breindl, C.; Müller, T. E. Eur. J. Inorg. Chem. 1999, 1121.
111. Xiao, D.; Zhang, X. Angew. Chem. Int. Ed. 2001, 40, 3425; Angew. Chem. 2001, 113, 3533.
112. Xiao, D.; Zhang, X. Angew. Chem. Int. Ed. 2001, 40, 3425; Angew. Chem. 2001, 113, 3533.
113. Herrera, V.; Munoz, B.; Landaeta, V.; Canudas, N. J. Mol. Catal. A: Chem. 2001, 174, 141.
114. Beller, M.; Thiel, O. R.; Trauthwein, H.; Hartung, C. G. Chem.-Eur. J. 2000, 6, 2513.
115. Trauthwein, H.; Tillack, A.; Beller, M. Chem. Commun. 1999, 2029.
116. (a) Schmerling, L.; Luvisi, J. P.; Welak, R. W. J. Am. Chem. Soc. 1956, 78, 2819.
117. (b) Kiji, J.; Nishimura, S.; Yoshikawa, S.; Sasakawa, E.; Furukawa, J. Bull. Chem. Soc. Jpn. 1974, 47, 2523.
118. Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds, Appendix; Chapman and Hall: London, 1986, Tables 1 and 3.
119. Hartung, C. G.; Tillack, A.; Trauthwein, H.; Beller, M. J. Org. Chem. 2001, 66, 6339.
120. Haggin, J. Chem. Eng. News 1993, 17, 23.
121. Tillack, A.; Rudloff, I.; Beller, M. Eur. J. Org. Chem. 2001, 523.
122. Beller, M.; Thiel, O. R.; Trauthwein, H. Synlett 1999, 243.