1,4-Bis(trimethylsilyl)-1,4-diaza-2,5-cyclohexadienes as strong salt-free reductants for generating low-valent early transition metals with electron-donating ligands

Journal of the American Chemical Society

Volumn 136, Issue 13, 2014, Pages 5161-5170

  Saito, Teruhiko ^a   Nishiyama, Haruka ^a   Tanahashi, Hiromasa ^a   Kawakita, Kento ^a   Tsurugi, Hayato ^a   Mashima, Kazushi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ELECTRONS; REDOX REACTIONS; SILICON COMPOUNDS; TRANSITION METAL COMPOUNDS;

CATALYTIC AMOUNTS; CATALYTIC REACTIONS; COUPLING REACTION; EARLY TRANSITION METALS; ELECTRON-DONATING LIGANDS; ETHYL 2-BROMOISOBUTYRATE; ORGANOSILICON COMPOUNDS; REFORMATSKY REACTION;

CHLORINE COMPOUNDS;

1,1' BIS(TRIMETHYLSILYL) 1,1 DIHYDRO 4,4' BIPYRIDINE; 1,4 BIS(TRIMETHYLSILYL) 1,4 DIAZA 2,5 CYCLOHEXADIENE DERIVATIVE; 2,3,5,6 TETRAMETHYL 1,4 BIS(TRIMETHYLSILYL) 1,4 DIAZA 2,5 CYCLOHEXADIENE; 2,5 DIMETHYL 1,4 BIS(TRIMETHYLSILYL) 1,4 DIAZA 2,5 CYCLOHEXADIENE; METAL COMPLEX; ORGANOSILICON DERIVATIVE; PYRAZINE; REDUCING AGENT; TETRAMETHYLPYRAZINE; TITANOCENE; TITANOCENE DICHLORIDE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERIC PRESSURE; CATALYSIS; ELECTRON TRANSPORT; HYDROLYSIS; IONIZATION; OXIDATION REDUCTION POTENTIAL; REACTION ANALYSIS; REDUCTION; REFORMATSKY REACTION; X RAY ANALYSIS;

EID: 84897541755     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja501313s     Document Type: Article

References (125)

1. Takai, K. Comprehensive Organometallic Chemistry III; Crabtree, R. H., Mingos, M. P., Eds.; Elsevier: Amsterdam, 2007; Vol. 11, p 39.
2. Hirao, T. Top. Curr. Chem. 2007, 279, 53
3. McMurry, J. E. Acc. Chem. Res. 1983, 16, 405
4. McMurry, J. E. Chem. Rev. 1989, 89, 1513
5. Carnahan, E. M.; Protasiewicz, J. D.; Lippard, S. J. Acc. Chem. Res. 1993, 26, 90
6. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124
7. Fürstner, A. Chem. Rev. 1999, 99, 991
8. Hirao, T. Synlett 1999, 175
9. Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835
10. Rosenthal, U.; Pellny, P.-M.; Kirchbauer, F. G.; Burlakov, V. V. Acc. Chem. Res. 2000, 33, 119
11. Rosenthal, U.; Burlakov, V. V.; Arndt, P.; Baumann, W.; Spannenberg, A. Organometallics 2003, 22, 884
12. Poli, R. Angew. Chem., Int. Ed. 2006, 45, 5058
13. McGuinness, D. S. Chem. Rev. 2011, 111, 2321
14. Agapie, T. Coord. Chem. Rev. 2011, 255, 861
15. Streuff, J. Synthesis 2013, 45, 281
16. Peters, J. C.; Mehn, M. P. Activation of Small Molecules; Wiley-VCH: Weinheim, 2006; pp 81-119.
17. Van Tamelen, E. E. Acc. Chem. Res. 1970, 3, 361
18. Fryzuk, M. D.; Johnson, S. A. Coord. Chem. Rev. 2000, 200, 379
19. Schrock, R. R. Acc. Chem. Res. 2005, 38, 955
20. Tanabe, Y.; Nishibayashi, Y. Coord. Chem. Rev. 2013, 257, 2551
21. Cossairt, B. M.; Piro, N. A.; Cummins, C. C. Chem. Rev. 2010, 110, 4164
22. Donahue, J. P. Chem. Rev. 2006, 106, 4747
23. Walter, M. D.; Tamm, M. Angew. Chem., Int. Ed. 2010, 49, 3264
24. Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468
25. Lipski, T. A.; Hilfiker, M. A.; Nelson, S. G. J. Org. Chem. 1997, 62, 4566
26. Gansäuer, A. Chem. Commun. 1997, 457
27. Gansäuer, A. Synlett 1997, 363
28. Gansäuer, A.; Moschioni, M.; Bauer, D. Eur. J. Org. Chem. 1998, 1923
29. Hirao, T.; Asahara, M.; Muguruma, Y.; Ogawa, A. J. Org. Chem. 1998, 63, 2812
30. Hirao, T.; Ogawa, A.; Asahara, M. Org. Synth. 2005, 81, 26
31. Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 2533
32. Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349
33. Rosales, A.; Oller-Lopez Juan, L.; Justicia, J.; Gansäuer, A.; Oltra, J. E.; Cuerva, J. M. Chem. Commun. 2004, 2628
34. Estévez, R. E.; Justicia, J.; Bazdi, B.; Fuentes, N.; Paradas, M.; Choquesillo-Lazarte, D.; Garcia-Ruiz, J. M.; Robles, R.; Gansäuer, A.; Cuerva, J. M.; Oltra, J. E. Chem.-Eur. J. 2009, 15, 2774
35. Justicia, J.; Sancho-Sanz, I.; ávarez-Manzaneda, E.; Oltra, J. E.; Cuerva, J. M. Adv. Synth. Catal. 2009, 351, 2295
36. Sgreccia, L.; Bandini, M.; Morganti, S.; Quintavalla, A.; Umani-Ronchi, A.; Cozzi, P. G. J. Organomet. Chem. 2007, 692, 3191
37. Estévez, R. E.; Paradas, M.; Millán, A.; Jiménez, T.; Robles, R.; Cuerva, J. M.; Oltra, J. E. J. Org. Chem. 2008, 73, 1616
38. Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785
39. Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787
40. Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182
41. Gansäuer, A.; Pierobon, M.; Bluhm, H. Angew. Chem., Int. Ed. 1998, 37, 101
42. Zhou, L.; Hirao, T. Tetrahedron 2001, 57, 6927
43. Streuff, J.; Feurer, M.; Bichovski, P.; Frey, G.; Gellrich, U. Angew. Chem., Int. Ed. 2012, 51, 8661
44. Komori, K.; Oshita, H.; Mizobe, Y.; Hidai, M. J. Am. Chem. Soc. 1989, 111, 1939
45. Tanaka, H.; Sasada, A.; Kouno, T.; Yuki, M.; Miyake, Y.; Nakanishi, H.; Nishibayashi, Y.; Yoshizawa, K. J. Am. Chem. Soc. 2001, 133, 3498
46. Chirik, P. J.; Henling, L. M.; Bercaw, J. E. Organometallics 2001, 20, 534
47. Yandulov, D. V.; Schrock, R. R. Science 2003, 301, 76
48. Bradley, C. A.; Veiros, L. F.; Pun, D.; Lobkovsky, E.; Keresztes, I.; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 16600
49. Hirotsu, M.; Fontaine, P. P.; Epshteyn, A.; Zavalij, P. Y.; Sita, L. R. J. Am. Chem. Soc. 2007, 129, 9284
50. Pun, D.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2008, 130, 6047
51. Pun, D.; Bradley, C. A.; Lobkovsky, E.; Keresztes, I.; Chirik, P. J. J. Am. Chem. Soc. 2008, 130, 14046
52. Knobloch, D. J.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2010, 132, 10553
53. Knobloch, D. J.; Lobkovsky, E.; Chirik, P. J. Nat. Chem. 2010, 2, 30
54. Fontaine, P. P.; Yonke, B. L.; Zavalij, P. Y.; Sita, L. R. J. Am. Chem. Soc. 2010, 132, 12273
55. Arashiba, K.; Miyake, Y.; Nishibayashi, Y. Nat. Chem. 2011, 3, 120
56. Tanaka, H.; Sasada, A.; Kouno, T.; Yuki, M.; Miyake, Y.; Nakanishi, H.; Nishibayashi, Y.; Yoshizawa, K. J. Am. Chem. Soc. 2011, 133, 3498
57. Semproni, S. P.; Milsmann, C.; Chirik, P. J. Organometallics 2012, 31, 3672
58. Semproni, S. P.; Knobloch, D. J.; Milsmann, C.; Chirik, P. J. Angew. Chem., Int. Ed. 2013, 52, 5372
59. Watanabe, T.; Ishida, Y.; Matsuo, T.; Kawaguchi, H. J. Am. Chem. Soc. 2009, 131, 3474
60. Reeds, J. P.; Yonke, B. L.; Zavalij, P. Y.; Sita, L. R. J. Am. Chem. Soc. 2011, 133, 18602
61. Bryan, J. C.; Geib, S. J.; Rheingold, A. L.; Mayer, J. M. J. Am. Chem. Soc. 1987, 109, 2826
62. Hall, K. A.; Mayer, J. M. J. Am. Chem. Soc. 1992, 114, 10402
63. Yonke, B. L.; Reeds, J. P.; Zavalij, P. Y.; Sita, L. R. Angew. Chem., Int. Ed. 2011, 50, 12342
64. Schrock, R. R.; Listemann, M. L.; Sturgeoff, L. G. J. Am. Chem. Soc. 1982, 104, 4291
65. Bryan, J. C.; Mayer, J. M. J. Am. Chem. Soc. 1987, 109, 7213
66. Bryan, J. C.; Mayer, J. M. J. Am. Chem. Soc. 1990, 112, 2298
67. Bryan, J. C.; Arterburn, J. B.; Cook, G. K.; Mayer, J. M. Organometallics 1992, 11, 3965
68. Tsai, Y.-C.; Johnson, M. J. A.; Mindiola, D. J.; Cummins, C. C. J. Am. Chem. Soc. 1999, 121, 10426
69. Sattler, A.; Parkin, G. Nature 2010, 463, 523
70. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877
71. Sekutowski, D. J.; Stucky, G. D. Inorg. Chem. 1975, 14, 2192
72. Enemærke, R. J.; Larsen, J.; Skrydstrup, T.; Daasbjerg, K. Organometallics 2004, 23, 1866
73. Enemærke, R. J.; Larsen, J.; Skrydstrup, T.; Daasbjerg, K. J. Am. Chem. Soc. 2004, 126, 7853
74. Handa, Y.; Inanaga, J. Tetrahedron Lett. 1987, 28, 5717
75. Larson, M. L.; Moore, F. W. Inorg. Chem. 1964, 3, 285
76. Allen, E. A.; Brisdon, B. J.; Fowles, G. W. A. J. Chem. Soc. 1964, 4531
77. Filippo, J. S.; Sowinski, A. F.; Romano, L. J. J. Am. Chem. Soc. 1975, 97, 1599
78. Kovacic, P.; Brace, N. O. J. Am. Chem. Soc. 1984, 76, 5491
79. Berglund, M.; Andersson, C.; Larsson, R. J. Organomet. Chem. 1986, 314, 61
80. Persson, C.; Andersson, C. Polyhedron 1991, 10, 2089
81. Persson, C.; Andersson, C. Inorg. Chim. Acta 1993, 203, 235
82. Theopold, K. H.; Holrnes, S. J.; Schrock, R. R. Angew. Chem., Int. Ed. Engl. 1983, 22, 1010
83. Hermes, A. R.; Giriolami, G. S. Inorg. Synth. 1998, 32, 309
84. Arteaga-Müller, R. A.; Tsurugi, H.; Saito, T.; Yanagawa, M.; Oda, S.; Mashima, K. J. Am. Chem. Soc. 2009, 131, 5370
85. Tsurugi, H.; Saito, T.; Tanahashi, H.; Arnold, J.; Mashima, K. J. Am. Chem. Soc. 2011, 133, 18673
86. Tsurugi, H.; Tanahashi, H.; Nishiyama, H.; Fegler, W.; Saito, T.; Sauer, A.; Okuda, J.; Mashima, K. J. Am. Chem. Soc. 2013, 135, 5986
87. Bock, H.; Kaim, W. Tetrahedron Lett. 1977, 27, 2343
88. Bock, H.; Kaim, W. J. Am. Chem. Soc. 1980, 102, 4429
89. Kaim, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 599
90. Kaim, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 600
91. Bock, H.; Kaim, W. Acc. Chem. Res. 1982, 15, 9
92. Kaim, W. Angew. Chem., Int. Ed. Engl. 1983, 22, 171
93. Kaim, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 613
94. Baumgarten, J.; Bessenbacher, C.; Kaim, W.; Stahl, T. J. Am. Chem. Soc. 1989, 111, 2126
95. Lichtblau, A.; Ehlend, A.; Hausen, H. D.; Kaim, W. Chem. Ber. 1995, 128, 745
96. Kaim, W. J. Am. Chem. Soc. 1983, 105, 707
97. Pattiasina, J. W.; van Bolhuis, F.; Teuben, J. H. Angew. Chem., Int. Ed. Engl. 1987, 26, 330
98. Kraft, S.; Hanuschek, E.; Beckhaus, R.; Haase, D.; Saak, W. Chem.-Eur. J. 2005, 11, 969
99. Enders, M.; Fink, J.; Maillant, V.; Pritzkow, H. Z. Anorg. Allg. Chem. 2001, 627, 2281
100. Battaglia, L. P.; Nardelli, M.; Pelizzi, C.; Predieri, G. J. Organomet. Chem. 1983, 259, 301
101. Langmaier, J.; Samec, Z.; Varga, V.; Horácek, M.; Mach, K. J. Organomet. Chem. 1999, 579, 348
102. Nieman, J.; Pattiasina, J. W.; Teuben, J. H. J. Organomet. Chem. 1984, 262, 157
103. Schofield, A. D.; Nova, A.; Selby, J. D.; Schwarz, A. D.; Clot, E.; Mountford, P. Chem.-Eur. J. 2011, 17, 265
104. Tran, B. L.; Washington, M. P.; Henckel, D. A.; Gao, X.; Park, H.; Pink, M.; Mindiola, D. J. Chem. Commun. 2012, 48, 1529
105. Unruangsri, J.; Morgan, H.; Schwarz, A. D.; Schofield, A. D.; Mountford, P. Organometallics 2013, 32, 3091
106. Hausen, H. D.; Mundt, H.; Kaim, W. J. Organomet. Chem. 1985, 296, 321
107. Mashima, K.; Matsuo, Y.; Tani, K. Organometallics 1999, 18, 1471
108. Ting, C.; Messerle, L. Inorg. Chem. 1989, 28, 173
109. Rothfuss, H.; Barry, J. T.; Huffman, J. C.; Caulton, K. G.; Chisholm, M. H. Inorg. Chem. 1993, 32, 4573
110. Kaim, W. J. Mol. Struct. (Theochem) 1984, 109, 277
111. Vlcek, P.; Havlas, Z.; Pavlicek, Z. Collect. Czech. Chem. Commun. 1999, 64, 633
112. Huang, K.-W.; Waymouth, R. M. J. Am. Chem. Soc. 2002, 124, 8200
113. Ehlend, A.; Hausen, H. D.; Kaim, W.; Lichtblau, A.; Schwarz, W. J. Organomet. Chem. 1995, 501, 283
114. Weyenberg, D. R.; Toporcer, L. H. J. Am. Chem. Soc. 1962, 84, 2843
115. Laguerre, M.; Dunogues, J.; Calas, R.; Duffaut, N. J. Organomet. Chem. 1976, 112, 49
116. Gorsich, R. D. J. Am. Chem. Soc. 1958, 80, 4744
117. Cardoso, A. M.; Clark, R. J. H.; Moorhouse, S. J. Chem. Soc., Dalton Trans. 1980, 1156
118. Sharp, P. R.; Bryan, J. C.; Mayer, J. M. Inorg. Synth. 1990, 28, 326
119. Rothfuss, H.; Barry, J. T.; Huffman, J. C.; Caulton, K. G.; Chisholm, M. H. Inorg. Chem. 1993, 32, 4573
120. Kliegman, J. M.; Barnes, R. K. J. Org. Chem. 1970, 35, 3140
121. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518
122. Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557
123. Sheldrich, G. M. Acta Crystallogr. 2008, A64, 112
124. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Polidori, G. J. Appl. Crystallogr. 1994, 27, 435
125. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837