Heavy grignard reagents: Challenges and possibilities of aryl alkaline earth metal compounds

Chemistry - A European Journal

Volumn 13, Issue 22, 2007, Pages 6292-6306

  Westerhausen, Matthias ^a   Gärtner, Martin ^a   Fischer, Reinald ^a   Langer, Jens ^a   Yu, Lian ^b   Reiher, Markus ^b  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b ETH ZURICH   (Switzerland)

Author keywords

Alkaline earth metals; Calcium; Direct synthesis; Grignard reaction; Organocalcium chemistry

Indexed keywords

CHEMICAL BONDS; DERIVATIVES; IODINE COMPOUNDS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

DIRECT SYNTHESIS; GRIGNARD REACTION; ORGANOCALCIUM CHEMISTRY;

LIGANDS;

EID: 34547582032     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700558     Document Type: Article

References (145)

1. D. Seyferth, Organometallics 2006, 25, 2-24.
2. D. Seyferth, Organometallics 2001, 20, 2940-2955.
3. C. Elschenbroich, A. Salzer, Organometallics: A Concise Introduction, 2nd ed., VCH, Weinheim, 1992.
4. F. Bickelhaupt, J. Organomet. Chem. 1994, 475, 1-14.
5. J. J. Eisch, Organometallics 2002, 21, 5439-5463.
6. B. J. Wakefield, Organomet. Chem. Rev. 1966, 1, 131-156.
7. H. Normant, Bull. Soc. Chim. Fr. 1972, 2161-2175.
8. Grignard Reagents New Developments (Ed.: H. G. Richey), Wiley, Chichester, 2000.
9. E. Beckmann, Ber. Dtsch. Chem. Ges. 1905, 38, 904-906.
10. H. Gilman, F. Schulze, J. Am. Chem. Soc. 1926, 48, 2463-2467.
11. B. G. Gowenlock, WE. Lindsell, J. Organomet. Chem. Libr. 1977, 1-73.
12. J. J. Eisch, R. B. King, Organometallic Synthesis, Vol. 2, Academic Press, New York, 1981, p. 101.
13. R. Zerger, G. Stucky, J. Organomet. Chem. 1974, 80, 7-17.
14. a) P. Jutzi, Adv. Organomet. Chem. 1986, 26, 217-295;
15. b) P. Jutzi, J. Organomet. Chem. 1990, 400, 1-17;
16. c) T. P. Hanusa, Polyhedron 1990, 9, 1345-1362;
17. d) T. P. Hanusa, Chem. Rev. 1993, 93, 1023-1036;
18. e) D. J. Burkey, T. P. Hanusa, Comments Inorg. Chem. 1995, 17, 41-77;
19. f) P. Jutzi, N. Burford in Metallocenes (Eds.:A. Togni, R. L. Halterman), Wiley-VCH, Weinheim 1998, Chapter 1, pp. 3-54;
20. g) M. L. Hays, T. P. Hanusa, Adv. Organomet. Chem. 1996, 40, 117-170;
21. h) P. Jutzi, N. Burford, Chem. Rev. 1999, 99, 969-990;
22. i) T. P. Hanusa, Organometallics 2002, 21, 2559-2571.
23. F. G. N. Cloke, P. B. Hitchcock, M. F. Lappert, G. A. Lawless, B. Royo, J. Chem. Soc. Chem. Commun. 1991, 724-726.
24. a) T. P. Hanusa, Coord. Chem. Rev. 2000, 210, 329-367;
25. b) M. Westerhausen, Angew. Chem. 2001, 113, 3063-3065;
26. Angew. Chem. Int. Ed. 2001, 40, 2975-2977;
27. c) J. S. Alexander, K. Ruhlandt-Senge, Eur. J. Inorg. Chem. 2002, 2761-2774.
28. M. Westerhausen, M. Gärtner, R. Fischer, J. Langer, Angew. Chem. 2007, 119, 1994-2001;
29. Angew. Chem. Int. Ed. 2007, 46, 1950-1956.
30. C. Eaborn, S. A. Hawkes, P. B. Hitchcock, J. D. Smith, Chem. Commun. 1997, 1961-1962.
31. a) F. Feil, S. Harder, Organometallics 2000, 19, 5010-5015;
32. b) S. Harder, F. Feil, A. Weeber, Organometallics 2001, 20, 1044-1046;
33. c) S. Harder, F. Feil, Organometallics 2002, 21, 2268-2274;
34. d) F. Feil, C. Müller, S. Harder, J. Organomet. Chem. 2003, 683, 56-63;
35. e) S. Harder, S. Müller, E. Hübner, Organometallics 2004, 23, 178-183.
36. V. Knapp, G. Müller, Angew. Chem. 2001, 113, 187-190;
37. Angew. Chem. Int. Ed. 2001, 40, 183-186.
38. a) J. S. Jakob, K. Ruhlandt-Senge, Angew. Chem. 2001, 113, 2732-2734;
39. Angew. Chem. Int. Ed. 2001, 40, 2658-2660;
40. b) J. S. Alexander, K. Ruhlandt-Senge, H. Hope, Organometallics 2003, 22, 4933-4937;
41. c) J. S. Alexander, K. Ruhlandt-Senge, Chem. Eur. J. 2004, 10, 1274-1280.
42. P. R. Markies, T. Nomoto, G. Schat, O. S. Akkerman, F. Bickelhaupt, W J. J. Smeets, A. L. Spek, Organometallics 1991, 10, 3826-3837.
43. a) K. Mochida, H. Ogawa, J. Organomet. Chem. 1983, 243, 131-135;
44. b) K. Mochida, Y. Hiraga, H. Takeuchi, H. Ogawa, Organometallics 1987, 6, 2293-2297.
45. J. P. Dunne, M. Tacke, C. Selinka, D. Stalke, Eur. J. Inorg. Chem. 2003, 1416-1425.
46. As one of the derivatization reactions, Dunne et al. described the reaction of aryl calcium hydride with a substituted phenole yielding a calcium bis(phenolate). However, activated calcium suspended in benzene would yield the same product.
47. S. Harder, J. Brettar, Angew. Chem. 2006, 118, 3554-3558;
48. Angew. Chem. Int. Ed. 2006, 45, 3474-3478.
49. S.-O. Hauber, F. Lissner, G. B. Deacon, M. Niemeyer, Angew. Chem. 2005, 117, 6021-6025;
50. Angew. Chem. Int. Ed. 2005, 44, 5871-5875.
51. N. Kawabata, A. Matsumura, S. Yamashita, Tetrahedron 1973, 29, 1069-1071.
52. a) W. C. Johnson, M. F. Stubbs, A. E. Sidwell, A. Pechukas, J. Am. Chem. Soc. 1939, 61, 318-329;
53. b) W. J. McCreary, J. Met. 1958, 10, 615-617;
54. c) J. Evers, A. Weiss, E. Kaldis, J. Muheim, J. Less-Common Met. 1973, 30, 83-95.
55. M. Westerhausen, Coord. Chem. Rev. 1998, 176, 157-210.
56. S. R. Drake, D. J. Otway, J. Chem. Soc. Chem. Commun. 1991, 517-519;
57. corrigendum: S. R. Drake, D. J. Otway, J. Chem. Soc. Chem. Commun. 1991, 1060.
58. H. Bönnemann, B. Bogdanovic, R. Brinkmann, N. Egeler, R. Benn, I. Topalovic, K. Seevogel, Main Group Met. Chem. 1990, 13, 341-362.
59. a) R. D. Rieke, Science 1989, 246, 1260-1264;
60. b) T.-C. Wu, H. Xiong, R. D. Rieke, J. Org. Chem. 1990, 55, 5045-5051;
61. c) M. J. Mc-Cormick, K. B. Moon, S. R. Jones, T P. Hanusa, J. Chem. Soc. Chem. Commun. 1990, 778-779.
62. K. J. Klabunde, Acc. Chem. Res. 1975, 8, 393-399.
63. R. Fischer, M. Gärtner, H. Görls, M. Westerhausen, Organometallics 2006, 25, 3496-3500.
64. a) W. Biltz, G. F. Hüttig, Z. Anorg. Allg. Chem. 1920, 114, 241-265;
65. b) R. Juza, H. Schumacher, Z. Anorg. Allg. Chem. 1963, 324, 278-286;
66. c) R. Juza, Angew. Chem. 1964, 76, 290-300;
67. Angew. Chem. Int. Ed. Engl. 1964, 3, 471-481;
68. d) N. Mammano, M. J. Sienko, J. Solid State Chem. 1970, 1, 534-535.
69. R. Fischer, M. Gärtner, H. Görls, M. Westerhausen, Angew. Chem. 2006, 118, 624-627;
70. Angew. Chem. Int. Ed. 2006, 45, 609-612.
71. M. Gärtner, H. Görls, M. Westerhausen, Synthesis 2007, 725-730.
72. R. Fischer, H. Görls, M. Westerhausen, Inorg. Chem. Commun. 2005, 5, 1159-1161.
73. M. Fossatelli, R. den Besten, H. D. Verkruijsse, L. Brandsma, Reel. Trav. Chim. Pays-Bas 1994, 113, 527-528.
74. G. Bruhat, V. Thomas, Compt. rend. 1926, 183, 297-299.
75. D. C. Bradley, M. B. Hursthouse, A. A. Ibrahim, K. M. Abdul Malik, M. Motevalli, R. Möseler, H. Powell, J. D. Runnacles, A. C. Sullivan, Polyhedron 1990, 9, 2959-2964.
76. C. Ruspic, S. Harder, Organometallics 2005, 24, 5506-5508.
77. M. Gärtner, H. Görls, M. Westerhausen, Organometallics 2007, 26, 1077-1083.
78. J. Langer, H. Görls, M. Westerhausen, unpublished results.
79. M. Gärtner, R. Fischer, J. Langer, H. Görls, D. Walther, M. Westerhausen, Inorg. Chem. 2007, 46, in press.
80. R. Fischer, M. Gärtner, H. Görls, L. Yu, M. Reiher, M. Westerhausen, Angew. Chem. 2007, 119, 1642-1647;
81. Angew. Chem. Int. Ed. 2007, 46, 1618-1623.
82. J. Langer, H. Görls, M. Westerhausen, Inorg. Chem. Commun. 2007, 10, in press.
83. B. Zobel, K. Jurkschat, Main Group Met. Chem. 1998, 21, 765-767;
84. see also: R. Altmann, O. Gausset, R. Hummeltenberg, K. Jurkschat, S. Kuhn, M. Schurmann, B. Zobel in Organosilicon Chemistry IV: From Molecules to Materials (Eds.: N. Auner, J. Weis), Wiley-VCH, Weinheim, 2000, p. 394-398.
85. a) M. Kaupp, Angew. Chem. 2001, 113, 3642-3677;
86. Angew. Chem. Int. Ed. 2001, 40, 3534-3565;
87. b) R. J. Gillespie, S. Noury, J. Pilmé, B. Silvi, Inorg. Chem. 2004, 43, 3248-3256.
88. M. Kaupp, P. von R. Schleyer, J. Am. Chem. Soc. 1992, 114, 491-497.
89. a) R. L. DeKock, M. A. Peterson, L. K. Timmer, E. J. Baerends, P. Vernooijs, Polyhedron 1990, 9, 1919-1934;
90. b) M. Kaupp, P. von R. Schleyer, H. Stoll, H. Preuss, J. Chem. Phys. 1991, 94, 1360-1366;
91. c) M. Kaupp, P. von R. Schleyer, J. Am. Chem. Soc. 1993, 115, 11202-11208.
92. R. J. Gillespie, E. A. Robinson, Angew. Chem. 1996, 108, 539-560;
93. Angew. Chem. Int. Ed. Engl. 1996, 35, 495-514.
94. a) I. Resa, E. Carmona, E. Gutierrez-Puebla, A. Monge, Science 2004, 305, 1136-1138;
95. b) D. del Río, A. Galindo, I. Resa, E. Carmona, Angew. Chem. 2005, 117, 1270-1273;
96. Angew. Chem. Int. Ed. 2005, 44, 1244-1247.
97. Z. Zhu, R. J. Wright, M. M. Olmstead, E. Rivard, M. Brynda, P. P. Power, Angew. Chem. 2006, 118, 5939-5942;
98. Angew. Chem. Int. Ed. 2006, 45, 5807-5810.
99. Z. Zhu, R. C. Fischer, J. C. Fettinger, E. Rivard, M. Brynda, P. P. Power, J. Am. Chem. Soc. 2006, 128, 15068-15069.
100. M. Reiher, L. Yu, M. Gärtner, M. Westerhausen, unpublished results.
101. M. Westerhausen, W. Schwarz, Z. Anorg. Allg. Chem. 1996, 622, 903-913.
102. a) P. B. Hitchcock, M. F. Lappert, G. A. Lawless, B. Royo, J. Chem. Soc. Chem. Commun. 1990, 1141-1143;
103. b) K. F. Tesh, T. P. Hanusa, J. C. Huffman, C. J. Huffman, Inorg. Chem. 1992, 31, 5572-5579.
104. a) E. O. Fischer, G. Stolzle, Chem. Ber. 1961, 94, 2187-2193;
105. b) M. Kirilov, G. Petrov, K. Angelov, J. Organomet. Chem. 1976, 113, 225-232;
106. c) M. J. McCormick, R. A. Williams, L. J. Levine, T. P. Hanusa, Polyhedron 1988, 7, 725-730.
107. a) F. W. Swamer, G. A. Reynolds, C. R. Hauser, J. Org. Chem. 1951, 16, 43-46;
108. b) J. J. Ritter, R. D. Anderson, J. Org. Chem. 1959, 24, 208-210.
109. M. Westerhausen, W. Schwarz, Z. Naturforsch. B 1992, 47, 453-459.
110. A. R. Utke, R. T. Sanderson, J. Org. Chem. 1964, 29, 1261-1264.
111. H. O. Fröhlich, Z. Chem. 1975, 15, 316-317.
112. a) Y. Joh, T. Yoshihara, Y. Kotake, Y Imai, S. Kurihara, J. Polym. Sci. Polym. Chem. Ed. 1967, 5, 2503-2522;
113. b) Y. Kotake, Y. Joh, F. Ide, J. Polym. Sci., Polym. Lett. Ed. 1970, 8, 101-106;
114. c) K. Hisatani, H. Ono, Jpn. Kokai Tokkyo Koho JP 87-236223 19870922;
115. d) K. Hisatani, H. Ono, Jpn. Kokai Tokkyo Koho, JP 88-26522 19880209;
116. e) E. S. Shamshoun, M. Lopez, H. Chen, Eur. Pat. Appl. 2000, EP 2000-200578 20000221.
117. M. Westerhausen, M. Gärtner, H. Görls, unpublished results.
118. R. R. Fraser, T. S. Mansour, S. Savard, J. Org. Chem. 1985, 50, 3232-3234.
119. M. Westerhausen, W. Schwarz, J. Organomet. Chem. 1993, 463, 51-63.
120. M. Westerhausen, C. Gückel, H. Piotrowski, M. Vogt, Z. Anorg. Allg. Chem. 2002, 628, 735-740.
121. M. Westerhausen, C. Gückel, T. Habereder, M. Vogt, M. Warchhold, H. Nöth, Organometallics 2001, 20, 893-899.
122. R. Fischer, H. Görls, M. Westerhausen, Organometallics 2007, 26, in press.
123. U. Cremer, S. Disch, U. Ruschewitz, Z. Anorg. Allg. Chem. 2004, 630, 2304-2310.
124. M. Westerhausen, Dalton Trans. 2006, 4755-4768.
125. a) D. J. Burkey, T. P. Hanusa, Organometallics 1996, 15, 4971-4976;
126. b) D. C. Green, U. Englich, K. Ruhlandt-Senge, Angew. Chem. 1999, 111, 365-367;
127. Angew. Chem. Int. Ed. 1999, 38, 354-357.
128. L. Orzechowski, G. Jansen, S. Harder, J. Am. Chem. Soc. 2006, 128, 14676-14684.
129. a) W. Teng, U. Englich, K. Ruhlandt-Senge, Angew. Chem. 2003, 115, 3789-3792;
130. Angew. Chem. Int. Ed. 2003, 42, 3661-3664;
131. b) W. Teng, K. Ruhlandt-Senge, Organometallics 2004, 23, 2694-2700.
132. See also: W. Teng, K. Ruhlandt-Senge, Chem. Eur. J. 2005, 11, 2462-2470.
133. a) Z. Zhong, P. J. Dijkstra, C. Birg, M. Westerhausen, J. Feijen, Macromolecules 2001, 34, 3863-3868;
134. b) Z. Zhong, S. Schneiderbauer, P. J. Dijkstra, M. Westerhausen, J. Feijen, J. Polym. Res. J. Polm. Environm. 2002, 9, 31-38;
135. c) M. Westerhausen, S. Schneiderbauer, A. N. Kneifel, Y. Söltl, P. Mayer, H. Nöth, Z. Zhong, P. J. Dijkstra, J. Feijen, Eur. J. Inorg. Chem. 2003, 3432-3439;
136. d) Z. Zhong, S. Schneiderbauer, P. J. Dijkstra, M. Westerhausen, J. Feijen, Polym. Bull. 2003, 51, 175-182.
137. a) M. H. Chisholm, J. Gallucci, K. Phomphrai, Chem. Commun. 2003, 48-49;
138. b) M. H. Chisholm, J. C. Gallucci, K. Phomphrai, Inorg. Chem. 2004, 43, 6717-6725.
139. a) R. Langer, Acc. Chem. Res. 2000, 33, 94-101;
140. b) K. Nakano, N. Kosaka, T. Hiyama, K. Nozaki, Dalton Trans. 2003, 4039-4050;
141. c) O. Dechy-Cabaret, B. Martin-Vaca, D. Bourissou, Chem. Rev. 2004, 104, 6147-6176;
142. d) J. Wu, T.-L. Yu, C.-T. Chen, C.-C. Lin, Coord. Chem. Rev. 2006, 250, 602-626.
143. K. B. Dillon, F. Mathey, J. F. Nixon, Phosphorus: The carbon Copy, Wiley, Chichester, 1998.
144. M. Westerhausen, M. H. Digeser, H. Nöth, T. Seifert, A. Pfitzner, J. Am. Chem. Soc. 1998, 120, 6722-6725.
145. M. Westerhausen, M. H. Digeser, H. Nöth, W. Ponikwar, T. Seifert, K. Polborn, Inorg. Chem. 1999, 38, 3207-3214.