Reactivity of tris(allyl)aluminum toward pyridine: Coordination versus carbometalation

Organometallics

Volumn 30, Issue 16, 2011, Pages 4409-4417

  Lichtenberg, Crispin ^a   Spaniol, Thomas P ^a   Okuda, Jun ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOMETALATION; DIHYDROPYRIDINES; ELECTROPHILES; ELECTROPHILICITY; ION PAIRS; NEUTRAL LIGANDS; SINGLE CRYSTAL X-RAY DIFFRACTION; TETRAKIS;

CROWN ETHERS; PYRIDINE; X RAY DIFFRACTION;

ALUMINUM;

EID: 80051741741     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200492f     Document Type: Article

References (128)

1. Mole, T. and Jeffrey, E. A. Organoaluminum Compounds; Elsevier: Amsterdam, 1972; pp 106-118.
2. Miyaura, N. and Maruoka, K. Group 13 (B, Al) Metal Compounds. In Synthesis of Organometallic Compounds; Komiya, S., Ed.; Wiley VCH: Chichester, 1997; pp 364-390.
3. Elschenbroich, C., Organometallchemie, 5 th ed.; Teubner: Wiesbaden, 2005; pp 108-122.
4. Davidson, N.; Brown, H. C. J. Am. Chem. Soc. 1942, 64, 316-324
5. Coates, G. E.; Graham, J. J. Chem. Soc. 1963, 233-237
6. Cohen, B. M.; Cullingworth, A. R.; Smith, J. D. J. Chem. Soc. A 1969, 2193-2196
7. Sen, B.; White, G. L. J. Inorg. Nucl. Chem. 1973, 35, 2207-2215
8. Robinson, G. H.; Pennington, W. T.; Lee, B.; Self, M. F.; Hrncir, D. C. Inorg. Chem. 1991, 30, 809-812
9. Watkins, C. L.; Krannich, L. K.; Schauer, S. J. Inorg. Chem. 1995, 34, 6228-6230
10. Niamh McMahon, C.; G. Bott, S.; R. Barron, A. J. Chem. Soc., Dalton Trans. 1997, 3129-3138
11. C. Bradley, D.; Coumbarides, G.; S. Harding, I.; E. Hawkes, G.; A. Maia, I.; Motevalli, M. J. Chem. Soc., Dalton Trans. 1999, 3553-3558
12. Styron, E. K.; Lake, C. H.; Schauer, S. J.; Watkins, C. L.; Krannich, L. K. Polyhedron 1999, 18, 1595-1602
13. Bezombes, J.-P.; Gehrhus, B.; Hitchcock, P. B.; Lappert, M. F.; Merle, P. G. Dalton Trans. 2003, 1821-1829
14. Fan, M.; Duesler, E. N.; Nöth, H.; Paine, R. T. Inorg. Chem. 2010, 49, 2983-2989
15. Lloyd, J. E.; Wade, K. J. Chem. Soc. 1965, 2662-2668
16. Jennings, J. R.; Lloyd, J. E.; Wade, K. J. Chem. Soc. 1965, 5083-5094
17. Fisher, J. D.; Wei, M.-Y.; Willett, R.; Shapiro, P. J. Organometallics 1994, 13, 3324-3329
18. Harlan, C. J.; Gillan, E. G.; Bott, S. G.; Barron, A. R. Organometallics 1996, 15, 5479-5488
19. Lee, C. H.; Lee, S. J.; Park, J. W.; Kim, K. H.; Lee, B. Y.; Oh, J. S. J. Mol. Catal. A: Chem. 1998, 132, 231-239
20. The adduct formed between nitriles and tris(amido)aluminum compounds has been calculated to be an intermediate: Dornan, P.; Rowley, C. N.; Priem, J.; Barry, S. T.; Burchell, T. J.; Woo, T. K.; Richeson, D. S. Chem. Commun. 2008, 3645-3647
21. Wade, K.; Wyatt, B. K. J. Chem. Soc. A 1967, 1339-1343
22. Klerks, J. M.; Stufkens, D. J.; Van Koten, G.; Vrieze, K. J. Organomet. Chem. 1979, 181, 271-283
23. Van Vliet, M. R. P.; Van Koten, G.; Rotteveel, M. A.; Schrap, M.; Vrieze, K.; Kojic-Prodic, B.; Spek, A. L.; Duisenberg, A. J. M. Organometallics 1986, 5, 1389-1394
24. Van Vliet, M. R. P.; Van Koten, G.; De Keijser, M. S.; Vrieze, K. Organometallics 1987, 6, 1652-1664
25. Hecht, E. Z. Anorg. Allg. Chem. 2001, 627, 2351-2358
26. Khalilov, L. M.; Parfenova, L. V.; Pechatkina, S. V.; Ibragimov, A. G.; Genet, J. P.; Dzhemilev, U. M.; Beletskaya, I. P. J. Organomet. Chem. 2004, 689, 444-453
27. Tsai, C.-F.; Chen, H.-J.; Chang, J.-C.; Hung, C.-H.; Lai, C.-C.; Hu, C.-H.; Huang, J.-H. Inorg. Chem. 2004, 43, 2183-2188
28. Feher, F. J.; Budzichowski, T. A.; Weller, K. J. Polyhedron 1993, 12, 591-599
29. Zhou, S.; Chuang, D.-W.; Chang, S.-J.; Gau, H.-M. Tetrahedron: Asymmetry 2009, 20, 1407-1412
30. Swift, H. E.; Poole, C. P.; Itzel, J. F. J. Chem. Phys. 1964, 68, 2509-2513
31. Henrickson, C. H.; Duffy, D.; Eyman, D. P. Inorg. Chem. 1968, 7, 1047-1051
32. Petrakis, L.; Swift, H. E. J. Chem. Phys. 1968, 72, 546-549
33. Greenwood, N. N.; Perkins, P. G.; Twentyman, M. E. J. Chem. Soc. A 1969, 249-253
34. Brown, T. L.; Murrell, L. L. J. Am. Chem. Soc. 1972, 94, 378-384
35. Seidel, W. Z. Anorg. Allg. Chem. 1985, 524, 101-105
36. Healy, M. D.; Ziller, J. W.; Barron, A. R. J. Am. Chem. Soc. 1990, 112, 2949-2954
37. Herron, N.; Thorn, D. L.; Harlow, R. L.; Davidson, F. J. Am. Chem. Soc. 1993, 115, 3028-3029
38. Sun, H.-S.; Wang, X.-M.; You, X.-Z.; Huang, X.-Y. Polyhedron 1995, 14, 2159-2163
39. van Poppel, L. H.; Bott, S. G.; Barron, A. R. J. Chem. Soc., Dalton Trans. 2002, 3327-3332
40. Voiculescu, N. Appl. Organomet. Chem. 2002, 16, 94-98
41. Thomas, F.; Bauer, T.; Schulz, S.; Nieger, M. Z. Anorg. Allg. Chem. 2003, 629, 2018-2027
42. Leszczynska, K.; Madura, I.; Kunicki, A. R.; Zachara, J. J. Organomet. Chem. 2006, 691, 5970-5979
43. Wrackmeyer, B.; Klimkina, E. V.; Ackermann, T.; Milius, W. Inorg. Chim. Acta 2009, 362, 3941-3948
44. Goldmann, S.; Stoltefuss, J. Angew. Chem., Int. Ed. 1991, 30, 1559-1578
45. Prokai, L.; Prokai-Tatrai, K.; Bodor, N. Med. Rese. Rev. 2000, 20, 367-416
46. Lavilla, R. J. Chem. Soc., Perkin Trans. 1 2002, 1141-1156
47. Visentin, S.; Rolando, B.; Di Stilo, A.; Fruttero, R.; Novara, M.; Carbone, E.; Roussel, C.; Vanthuyne, N.; Gasco, A. J. Med. Chem. 2004, 47, 2688-2693
48. Litvic, M.; Cepanec, I.; Filipan, M.; Kos, K.; Bartolincic, A.; Druskovic, V.; Tibi, M. M.; Vinkovic, V. Heterocycles 2005, 65, 23-35
49. Schlosser, M.; Mongin, F. Chem. Soc. Rev. 2007, 36, 1161-1172
50. Zhou, Y.-G. Acc. Chem. Res. 2007, 40, 1357-1366
51. Soboleski, D. A.; Li-Kwong-Ken, M. C.; Wynn, H.; Triggle, C. R.; Wolowyk, M. W.; Knaus, E. E. Drug Des. Delivery 1988, 2, 177-189
52. Ziegler, K.; Zeiser, H. Ber. Dtsch. Chem. Ges. 1930, 63, 1847-1851
53. Gilman, H.; Eisch, J.; Soddy, T. J. Am. Chem. Soc. 1957, 79, 1245-1249
54. Abramovitch, R. A.; Poulton, G. A. Chem. Commun. 1967, 274-275
55. Comins, D. L.; Abdullah, A. H. J. Org. Chem. 1982, 47, 4315-4319
56. Yamaguchi, R.; Nakazono, Y.; Kawanisi, M. Tetrahedron Lett. 1983, 24, 1801-1804
57. Barr, D.; Snaith, R.; Mulvey, R. E.; Reed, D. Polyhedron 1988, 7, 665-668
58. Armstrong, D. R.; Mulvey, R. E.; Barr, D.; Snaith, R.; Reed, D. J. Organomet. Chem. 1988, 350, 191-205
59. Elschenbroich, C. Organometallchemie, 5 th ed.; Teubner: Wiesbaden, 2005.
60. Jochmann, P.; Dols, T. S.; Spaniol, T. P.; Perrin, L.; Maron, L.; Okuda, J. Angew. Chem., Int. Ed. 2010, 49, 7795-7798
61. Khartabil, H. K.; Gros, P. C.; Fort, Y.; Ruiz-López, M. F. J. Am. Chem. Soc. 2010, 132, 2410-2416
62. Piers, E.; Soucy, M. Can. J. Chem. 1974, 52, 3563-3564
63. Akiba, K.-y.; Iseki, Y.; Wada, M. Bull. Chem. Soc. Jpn. 1984, 57, 1994-1999
64. Comins, D. L.; Brown, J. D. Tetrahedron Lett. 1984, 25, 3297-3300
65. Mangeney, P.; Gosmini, R.; Raussou, S.; Commercon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877-1888
66. Scollard, J. D.; McConville, D. H.; Vittal, J. J. Organometallics 1997, 16, 4415-4420
67. Bailey, B. C.; Fan, H.; Huffman, J. C.; Baik, M.-H.; Mindiola, D. J. J. Am. Chem. Soc. 2006, 128, 6798-6799
68. Krut'ko, D. P.; Kirsanov, R. S.; Belov, S. A.; Borzov, M. V.; Churakov, A. V.; Howard, J. A. K. Polyhedron 2007, 26, 2864-2870
69. Begum, R.; Komuro, T.; Tobita, H. Chem. Lett. 2007, 36, 650-651
70. Cámpora, J.; Pérez, C. M.; Rodríguez-Delgado, A.; Naz, A. M.; Palma, P.; Álvarez, E. Organometallics 2007, 26, 1104-1107
71. Danopoulos, A. A.; Pugh, D.; Wright, J. A. Angew. Chem., Int. Ed. 2008, 47, 9765-9767
72. Zuhayra, M.; Lützen, U.; Lützen, A.; Papp, L.; Henze, E.; Friedrichs, G.; Oberdorfer, F. Inorg. Chem. 2008, 47, 10177-10182
73. Fout, A. R.; Bailey, B. C.; Buck, D. M.; Fan, H.; Huffman, J. C.; Baik, M.-H.; Mindiola, D. J. Organometallics 2010, 29, 5409-5422
74. Thompson, M. E.; Baxter, S. M.; Bulls, A. R.; Burger, B. J.; Nolan, M. C.; Santarsiero, B. D.; Schaefer, W. P.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 203-219
75. Deelman, B.-J.; Stevels, W. M.; Teuben, J. H.; Lakin, M. T.; Spek, A. L. Organometallics 1994, 13, 3881-3891
76. Duchateau, R.; van Wee, C. T.; Teuben, J. H. Organometallics 1996, 15, 2291-2302
77. Bambirra, S.; Boot, S. J.; van Leusen, D.; Meetsma, A.; Hessen, B. Organometallics 2004, 23, 1891-1898
78. Arndt, S.; Elvidge, B. R.; Zeimentz, P. M.; Spaniol, T. P.; Okuda, J. Organometallics 2005, 25, 793-795
79. Jantunen, K. C.; Scott, B. L.; Gordon, J. C.; Kiplinger, J. L. Organometallics 2007, 26, 2777-2781
80. Pool, J. A.; Scott, B. L.; Kiplinger, J. L. J. Alloys Compd. 2006, 418, 178-183
81. Kiplinger, J. L.; Scott, B. L.; Schelter, E. J.; Pool Davis Tournear, J. A. J. Alloys Compd. 2007, 444-445, 477-482
82. Castro, L.; Yahia, A.; Maron, L. Dalton Trans. 2010, 39, 6682-6692
83. Brüser, W.; Schröder, S.; Witke, K. Z. Anorg. Allg. Chem. 1976, 421, 89-96
84. Focante, F.; Camurati, I.; Resconi, L.; Guidotti, S.; Beringhelli, T.; D'Alfonso, G.; Donghi, D.; Maggioni, D.; Mercandelli, P.; Sironi, A. Inorg. Chem. 2006, 45, 1683-1692
85. Hashimoto, Y.; Nagai, A.; Banno, T.; Umeno, M. JP 2003238572 (A), Aug 27, 2003.
86. Kaszynski, P.; Pakhomov, S.; Gurskii, M. E.; Erdyakov, S. Y.; Starikova, Z. A.; Lyssenko, K. A.; Antipin, M. Y.; Young, V. G.; Bubnov, Y. N. J. Org. Chem. 2009, 74, 1709-1720
87. Beachley, O. T.; Mosscrop, M. T.; Churchill, M. R. J. Organomet. Chem. 2001, 626, 59-67
88. Jutzi, P.; Sielemann, H.; Neumann, B.; Stammler, H.-G. Inorg. Chim. Acta 2005, 358, 4208-4216
89. Tyrra, W.; Wickleder, M. S. J. Organomet. Chem. 2003, 677, 28-34
90. Sun, H.-S.; Wang, X.-M.; Liu, Y.-J.; Huang, X.-Y.; You, X.-Z. J. Coord. Chem. 1996, 39, 265-271
91. Leman, J. T.; Roman, H. A.; Barron, A. R. Organometallics 1993, 12, 2986-2990
92. Uson, R.; Laguna, A.; Abad, J. A.; de Jesus, E. J. Chem. Soc., Dalton Trans. 1983, 1127-1130
93. Deacon, G. B.; Phillips, R. J. Aust. J. Chem. 1978, 31, 1709-1724
94. Numata, S.; Kurosawa, H.; Okawara, R. J. Organomet. Chem. 1975, 102, 259-263
95. Naumann, D.; Strauss, W.; Tyrra, W. J. Organomet. Chem. 1991, 407, 1-15
96. Bubnov, Y. N. Pure Appl. Chem. 1994, 66, 235-244
97. Bubnov, Y.; Demina, E.; Ignatenko, A. Russ. Chem. Bull. 1997, 46, 606-607
98. Wang, Z.-X.; Li, Y.-X. Organometallics 2003, 22, 4900-4904
99. Knijnenburg, Q.; Smits, J. M. M.; Budzelaar, P. H. M. Organometallics 2006, 25, 1036-1046
100. 4 react with pyridine to form 1,4-DHPs: Hensen, K.; Lemke, A.; Stumpf, T.; Bolte, M.; Fleischer, H.; Pulham, C. R.; Gould, R. O.; Harris, S. Inorg. Chem. 1999, 38, 4700-4704
101. A case of organoaluminum reagents generated in situ reacting with in situ formed ammonium salts to form 1,4-DHPs has also been reported: Hoberg, H. Liebigs Ann. Chem. 1967, 709, 123-134
102. Redox-induced coupling of pyridine (derivatives) coordinated to organoaluminum fragments leads to bis-1,4-DHPs: Dorogy, W. E.; Schram, E. P. Inorg. Chim. Acta 1983, 73, 31-35
103. Kaim, W. J. Organomet. Chem. 1983, 241, 157-169
104. Lichtenberg, C.; Robert, D.; Spaniol, T. P.; Okuda, J. Organometallics 2010, 29, 5714-5721
105. -1: Thomas, S.; Reynolds, W. L. J. Chem. Phys. 1966, 44, 3148-3149
106. Richardson, D.; Alger, T. D. J. Chem. Phys. 1975, 79, 1733-1739
107. Waver, I. Adv. Mol. Relax. Interact. 1982, 23, 269-271
108. One heteroleptic aluminum complex bearing allyl ligands has been reported and shows a coordination number of five: Schumann, H.; Kaufmann, J.; Dechert, S.; Schmalz, H.-G. Tetrahedron Lett. 2002, 43, 3507-3511
109. Burford, N.; Royan, B. W.; Spence, R. E. v. H.; Cameron, T. S.; Linden, A.; Rogers, R. D. J. Chem. Soc., Dalton Trans. 1990, 1521-1528
110. Linnert, M.; Bruhn, C.; Schmidt, H.; Herzog, R.; Steinborn, D. Polyhedron 2008, 27, 151-156
111. Roger, M.; Belkhiri, L.; Thuéry, P.; Arliguie, T.; Fourmigué, M.; Boucekkine, A.; Ephritikhine, M. Organometallics 2005, 24, 4940-4952
112. Roger, M.; Belkhiri, L.; Arliguie, T.; Thuéry, P.; Boucekkine, A.; Ephritikhine, M. Organometallics 2007, 27, 33-42
113. Gerteis, R. L.; Dickerson, R. E.; Brown, T. L. Inorg. Chem. 1964, 3, 872-875
114. Michel, O.; Meermann, C.; Törnroos, K. W.; Anwander, R. Organometallics 2009, 28, 4783-4790
115. Venugopal, A.; Kamps, I.; Bojer, D.; Berger, R. J. F.; Mix, A.; Willner, A.; Neumann, B.; Stammler, H.-G.; Mitzel, N. W. Dalton Trans. 2009, 5755-5765
116. Zimmermann, M.; Anwander, R. Chem. Rev. 2010, 110, 6194-6259
117. Bojer, D.; Venugopal, A.; Neumann, B.; Stammler, H.-G.; Mitzel, N. W. Angew. Chem., Int. Ed. 2010, 49, 2611-2614
118. Hong, J.; Zhang, L.; Yu, X.; Li, M.; Zhang, Z.; Zheng, P.; Nishiura, M.; Hou, Z.; Zhou, X. Chem.-Eur. J. 2011, 17, 2130-2137
119. Bojer, D.; Neumann, B.; Stammler, H.-G.; Mitzel, N. W. Chem.-Eur. J. 2011, 17, 6239-6247
120. Bojer, D.; Venugopal, A.; Mix, A.; Neumann, B.; Stammler, H.-G.; Mitzel, N. W. Chem.-Eur. J. 2011, 17, 6248-6255
121. Michel, O.; Törnroos, K. W.; Maichle-Mössmer, C.; Anwander, R. Chem.-Eur. J. 2011, 17, 4964-4967
122. Occhipinti, G.; Meermann, C.; Dietrich, H. M.; Litlabø, R.; Auras, F.; Törnroos, K. W.; Maichle-Mössmer, C. c.; Jensen, V. R.; Anwander, R. J. Am. Chem. Soc. 2011, 133, 6323-6337
123. Michel, O.; Yamamoto, K.; Tsurugi, H.; Maichle-Mössmer, C.; Törnroos, K. W.; Mashima, K.; Anwander, R., Organometallics 2011, DOI: 10.1021/om200361m.
124. Re-aromatization is a known phenomenon in the chemistry of metalated and nonmetalated DHPs; see e.g.: Hill, M. D. Chem.-Eur. J. 2010, 16, 12052-12062
125. Wänninen, E.; Ringbom, A. Anal. Chim. Acta 1955, 12, 308-318
126. Malissa, H.; Kotzian, H. Anal. Chim. Acta 1962, 26, 128-133
127. ASTRO, SAINT, and SADABS, Data Collection and Processing Software for the SMART System; Siemens: Madison, WI, 1996.
128. Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement; Göttingen, 1997.