Alkylation of iridium via tandem carbon-hydrogen bond activation/decarbonylation of aldehydes. Access to complexes with tertiary and highly hindered metal-carbon bonds

Organometallics

Volumn 19, Issue 11, 2000, Pages 2130-2143

  Alaimo, Peter J ^a   Arndtsen, Bruce A ^a   Bergman, Robert G ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000218892     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9910064     Document Type: Article

References (164)

1. Hill, C. L. Activation and Functionalization of Alkanes; Wiley: New York, 1989; pp 372. For recent reviews on C-H activation see refs 2-9.
2. Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 2181-2192.
3. Sen, A. Acc. Chem. Res. 1998, 31, 550-557.
4. Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879-2932.
5. Lohrenz, J. C. W.; Jacobsen, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1305-1307.
6. Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Two Volumes; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: New York, 1996; Vol. 2, pp 1081-1092, and references therein.
7. Schneider, J. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1069-1075.
8. Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154-162.
9. Schröder, D.; Schwarz, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1973-1995.
10. Periana, R. A.; Taube, D. J.; Gamble, S.; Taube, H.; Satoh, T.; Fujii, H. Science 1998, 280, 560-564.
11. Periana, R. A.; Taube, D. J.; Evitt, E. R.; Loffler, D. G.; Wentrcek, P. R.; Voss, G.; Masuda, T. Science 1993, 259, 340-343.
12. Johansson, L.; Ryan, O. B.; Tilset, M. J. Am. Chem. Soc. 1999, 121, 1974-1975.
13. Mylvaganam, K.; Bacskay, G. B.; Hush, N. S. J. Am. Chem. Soc. 1999, 227, 4633-4639.
14. Arndtsen, B. A.; Bergman, R. G. Science 1995, 270, 1970-1973.
15. Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462-10463.
16. Adamson, D. R.; Arndtsen, B. A.; Bergman, R. G. Manuscript in preparation.
17. Arndtsen, B. A.; Bergman, R. G. J. Organomet. Chem. 1995, 504, 143-146.
18. Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517-2518.
19. Luecke, H. F.; Bergman, R. G. J. Am. Chem. Soc. 1998, 120, 11008-11009.
20. A portion of the work described here has been reported in preliminary form: Alaimo, P. J.; Arndtsen, B. A.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 5269-5270.
21. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; pp 110-117.
22. 23,27-30
23. Lenges, C. P.; Brookhart, M.; White, P. S. Angew. Chem., Int. Ed. Engl. 1999, 38, 552-555.
24. Hinderling, C.; Feichtinger, D.; Plattner, D. A.; Chen, P. J. Am. Chem. Soc. 1997, 119, 10793-10804.
25. Hinderling, C.; Plattner, D. A.; Chen, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 243-244.
26. Luecke, H. F.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 11538-11539.
27. Wang, Y.; Agbossou, F.; Dalton, D. M.; Liu, Y. M.; Arif, A. M.; Gladysz, J. A. Organometallics 1993, 12, 2699-2713.
28. Gladysz, J. A.; Boone, B. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 551-583.
29. Cicero, R. L.; Protasiewicz, J. D. Organometallics 1995, 14, 4792-4798.
30. Helberg, L. E.; Gunnoe, T. B.; Brooks, B. C.; Sabat, M.; Harman, W. D. Organometallics 1999, 18, 573-581.
31. Song, J. S.; Szalda, D. J.; Bullock, R. M. Inorg. Chim. Acta 1997, 259, 161-172.
32. Mancuso, A. J.; Swern, D. Synthesis 1981, 165-185.
33. We also performed thermal decarbonylation reactions of several complexes using trimethylamine N-oxide; however, these reactions were less clean than the photoinitiated reactions.
34. Reduction of transition-metal carbonyl ligands to formyl, hydroxymethyl, and methyl ligands has been observed before. For leading references, see refs 35-36.
35. Berke, H.; Weiler, G. Angew. Ckem., Int. Ed. Engl. 1982, 21, 150-151.
36. Thorn, D. L. J. Am. Chem. Soc. 1980, 102, 7109-7110.
37. Buchanan, J. M.; Stryker, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 1537-1550.
38. Diversi, P.; Iacoponi, S.; Ingrosso, G.; Laschi, F.; Lucherini, A.; Zanello, P. J. Chem. Soc., Dalton Trans. 1993, 351-352.
39. The scarcity of reported formyl and hydroxymethyl complexes synthesized by reduction of a CO ligand is due to the ease by which these complexes undergo further reduction. For recent examples of transition-metal formyl complexes see refs 40-49.
40. Gladysz, J. A. Adv. Organomet. Chem. 1982, 20, 1-38.
41. Gibson, D. H.; Ding, Y.; Andino, J. G.; Mashuta, M. S.; Richardson, J. F. Organometallics 1998, 17, 5178-5183.
42. Söderberg, B. C.; Berry, A. K.; Jones, P. C. Organometallics 1898, 17, 1069-1078.
43. Wei, M. L.; Wayland, B. B. Organometallics 1996, 15, 4681-4683.
44. Fryzuk, M. D.; Mylvaganam, M.; Zaworotko, M. J.; Macgillivray, L. E. Organometallics 1996, 15, 1134-1138.
45. Guillevic, M. A.; Brégaint, P.; Lapinte, C. J. Organomet. Chem. 1996, 514, 157-162.
46. Toyohara, K.; Nagao, H.; Mizukawa, T.; Tanaka, K. Inorg. Chem. 1995, 34, 5399-5400.
47. Bunn, A. G.; Wei, M. L.; Wayland, B. B. Organometallics 1994, 13, 3390-3392.
48. Anderson, D. J.; Eisenberg, R. Inorg. Chem. 1994, 33, 5378-5379.
49. Chang, S.; White, P. S.; Brookhart, M. Organometallics 1993, 12, 3636-3644.
50. 52
51. Faller, J. W.; Ma, Y.; Smart, C. J.; DiVerdi, M. J. J. Organomet. Chem. 1991, 420, 237-252.
52. Stark, G. A.; Gladysz, J. A. Inorg. Chim. Acta 1998, 269, 167-180 and references therein.
53. Tolman, C. A.; Ittel, S. D.; English, A. D.; Jesson, J. P. J. Am. Chem. Soc. 1979, 101, 1742-1751.
54. Ozawa, F.; Yamagami, I.; Yamamoto, A. J. Organomet. Chem. 1994, 473, 265-272.
55. Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286-1291.
56. Lehmkuhl, H.; Schwickardi, R.; Mehler, G.; Krüger, C.; Goddard, R. Z. Anorg. Allg. Chem. 1991, 606, 141-155.
57. Arce, A. J.; De Sanctis, Y.; Deeming, A. J. J. Organomet. Chem. 1986, 311, 371-378.
58. Hardcastle, K. I.; Minassiam, H.; Arce, A. J.; De Sanctis, Y.; Deeming, A. J. J. Organomet. Chem. 1989, 368, 119-130.
59. Brown, K. L.; Clark, G. R.; Headford, C. E. L.; Marsden, K.; Roper, W. R. J. Am. Chem. Soc. 1979, 101, 503-505.
60. Bianchini, C.; Meli, A.; Peruzzini, M.; Vacca, A.; Zanobini, F. Organometallics 1987, 6, 2453-2455.
61. Bianchini, C.; Meli, A.; Peruzzini, M.; Ramirez, J. A.; Vacca, A.; Vizza, F.; Zanobini, F. Organometallics 1989, 8, 337-345.
62. Marder, T. B.; Roe, D. C.; Milstein, D. Organometallics 1988, 7, 1451-1453.
63. Milstein, D. Organometallics 1982, 1, 1549-1551.
64. Bianchini, C.; Meli, A.; Peruzzini, M.; Vizza, F.; Bachechi, F. Organometallics 1991, 10, 820-823.
65. Milstein, D. Chem. Commun. 1982, 1357-1358.
66. Ko, J.; Joo, W.-C. Bull. Korean Chem. Soc. 1987, 8, 372-376.
67. Gómez, M.; Kisenyi, J. M.; Sunley, G. J.; Maitlis, P. M. J. Organomet. Chem. 1985, 296, 197-207.
68. Gutiérrez-Puebla, E.; Monge, A.; Paneque, M.; Poveda, M. L.; Salazar, V.; Carmona, E. J. Am. Chem. Soc. 1999, 121, 248-249.
69. Bernard, K. A.; Atwood, J. D. Organometallics 1988, 7, 235-236.
70. Bernard, K. A.; Atwood, J. D. Organometallics 1989, 8, 795-800.
71. Landvatter, E. F.; Rauchfuss, T. R. Organometallics 1982, 1, 506-513.
72. Rauchfusa, T. B. J. Am. Chem. Soc. 1979, 101, 1045-1047.
73. Thorn, D. L. J. Mol. Catal. 1982, 17, 279-288.
74. Koh, J. J.; Lee, W.-H.; Willard, P. G.; Risen, W. M., Jr. J. Organomet. Chem. 1985, 284, 409-419.
75. Cornils, B.; Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Two Volumes; VCH: New York, 1996; Vols. 1-2, pp 194-196, 1085.
76. Simpson, M. C.; Colehamilton, D. J. Coord. Chem. Rev. 1996, 155, 163-207.
77. Frohning, C. D.; Kohlpaintner, C. W. In Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Two Volumes; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: New York, 1996; Vol. 1, pp 29-104.
78. Pino, P.; Piacenti, F.; Bianchi, M. In Organic Synthesis via Metal Carbonyls; Wender, I., Pino, P., Eds.; Interscience Publishers: New York, 1977; Vol. 2, pp 43-231.
79. See ref 21, pp 621-632.
80. Cornils, B.; Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Two Volumes; VCH: New York, 1996; Vol. 1, pp 195, 205.
81. Doughty, D. H.; Pignolet, L. H. In Homogeneous Catalysis with Metal Phosphine Complexes; Pignolet, L. H., Ed.; Plenum Press: New York, 1983; pp 343-375.
82. See ref 21, pp 362-365, 642-643, 768-775.
83. Tsuji, J.; Ohno, K. Tetrahedron Lett. 1967, 23, 2173-2176.
84. Ohno, K.; Tsuji, J. J. Am. Chem. Soc. 1968, 90, 99-107.
85. Walborsky, H. M.; Allen, L. E. Tetrahedron Lett. 1970, 11, 823-824.
86. Walborsky, H. M.; Allen, L. E. J. Am. Chem. Soc. 1971, 93, 5465-5468.
87. Suggs, J. W. J. Am. Chem. Soc. 1978, 100, 640-641.
88. Doughty, D. H.; Pignolet, L. H. J. Am. Chem. Soc. 1978, 100, 7083-7085.
89. Baldwin, J. E.; Barden, T. C.; Pugh, R. L.; Widdison, W. C. J. Org. Chem. 1987, 52, 3303-3307.
90. Abu-Hasanayn, F.; Goldman, M. E.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 2520-2524.
91. O'Connor, J. M.; Ma, J. J. Org. Chem. 1992, 57, 5075-5077.
92. Hawthorne, J. O.; Wilt, M. H. J. Org. Chem. 1960, 25, 2215-2216.
93. Domazetis, G.; Tarpey, B.; Dolphin, D.; James, B. R. J. Chem. Soc., Chem. Commun, 1980, 939-940.
94. Kovacs, I.; Szalontai, G.; Ungvary, F. J. Organomet. Chem. 1998, 524, 115-123.
95. Dennis, M.; Kolattukudy, P. E. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 5306-5310.
96. Dennis, M. W.; Kolattukudy, P. E. Arch. Biochem. Biophys. 1991, 287, 268-275.
97. Castellani, C. B.; Carugo, O.; Giusti, M.; Leopizzi, C.; Perotti, A.; Invernizzi, A. G.; Vidari, G. Tetrahedron 1996, 52, 11045-11052.
98. Alaimo, P. J.; Bergman, R. G. Organometallics 1999, 18, 2707-2717.
99. Klei, S. R.; Bergman, R. G.; Tilley, T. D. J. Am. Chem. Soc. 2000, 122, 1816-1817.
100. Strout, D. L.; Zaric, S.; Niu, S.; Hall, M. B. J. Am. Chem. Soc. 1996, 118, 6068-6069.
101. Bower, B. K.; Tennent, H. G. J. Am. Chem. Soc. 1972, 94, 2512-2514.
102. Kruse, W. J. Organomet. Chem. 1972, 42, C39-C42.
103. Gill, D. F.; Shaw, B. L. J. Chem. Soc., Chem. Commun. 1972, 65-66.
104. Buchwald, S. L.; Kreutzer, K. A.; Fisher, R. A. J. Am. Chem. Soc. 1990, 112, 4600-4601.
105. Nöth, H.; Schmidt, M. Organometallics 1995, 14, 4601-4610.
106. Bougeard, P.; McCullough, J. J.; Sayer, B. G.; McGlinchey, M. J. Inorg. Chim. Acta 1984, 89, 133-138.
107. Abrahamson, H. B.; Brandenburg, K. L.; Lucero, B.; Martin, M. E.; Dennis, E. Organometallics 1984, 3, 1379-1386.
108. Girolami, G. S.; Howard, C. G.; Wilkinson, G.; Dawes, H. M.; Thornton-Pett, M.; Motevalli, M.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1985, 921-929.
109. Giering, W. P.; Rosenblum, M. J. Organomet. Chem. 1970, 25, C71-C73.
110. Pannell, K. H.; Giasolli, T.; Kapoor, R. N. J. Organomet. Chem. 1986, 376, 315-318.
111. Schumann, H.; Jeske, G. Z. Naturforsch., B 1985, 1490-1494.
112. Byrne, E. K.; Richeson, D. S.; Theopold, K. H. J. Chem. Soc., Chem. Commun. 1986, 1491-1492.
113. Lehmkuhl, H.; Dimitrov, V. J. Organomet. Chem. 1996, 519, 69-73.
114. Lehmkuhl, H.; Dimitrov, V. J. Organomet. Chem. 1996, 519, 83-85.
115. Weydert, M.; Brennan, J. G.; Andersen, R. A.; Bergman, R. G. Organometallics 1995, 14, 3942-3951.
116. Kolodziej, R. M.; Schrock, R. R.; Davis, W. M. Inorg. Chem. 1988, 27, 3253-3255.
117. Ogoshi, H.; Watanabe, E.; Koketsu, N.; Yoshida, Z. Bull. Chem. Soc., Jpn. 1976, 49, 2529-2536.
118. Bresciani-Pahor, N.; Marzilli, L. G.; Randaccio, L.; Toscano, P. J.; Zangrando, E. J. Chem. Soc., Chem. Commun. 1984, 1508-1510.
119. Bresciani-Pahor, N.; Randaccio, L.; Zangrando, E.; Summers, M. F.; Ramsden, J. H., Jr.; Marzilli, P. A.; Marzilli, L. G. Organometallics 1985, 4, 2086-2090.
120. Geremia, S.; Randaccio, L.; Zangrando, E.; Antolino, L. J. Organomet. Chem. 1992, 425, 131-139.
121. Eckert, H.; Lenoir, D.; Ugi, I. J. Organomet. Chem. 1977, 141, C23-C27.
122. Brescianai-Pahor, N.; Randaccio, L.; Zangrando, E.; Marzilli, P. A. J. Chem. Soc., Dalton Trans. 1989, 1941-1946.
123. Geremia, S.; Randaccio, L.; Zangrando, E.; Marzilli, P. A. J. Organomet. Chem. 1992, 425, 131-139.
124. Brescianai-Pahor, N.; Attia, W. M.; Randaccio, L.; Lopez, C.; Charland, J.-P. Acta Crystallogr., Sect. C 1987, 43, 1484-1487.
125. Jensen, F. R.; Buchanan, D. H. J. Chem. Soc., Chem. Commun. 1973, 153-154.
126. Giese, B.; Hartung, J.; Kesselheim, C.; Lindner, H. J.; Svoboda, I. Chem. Ber. 1993, 126, 1193-1200.
127. Our group prepared the first and only known tertiary alkyl iridium complex, a cubyl iridium species, hut did not isolate it: Sponsler, M. B.; Weiller, B. H.; Stoutland, P. O.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 6841-6843.
128. 3-1,1-dimethylallyl)iridium complex: Penana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7346-7355.
129. Lehmkuhl, H.; Mehler, G. Chem. Ber. 1985, 118, 2407-2417.
130. Lehmkuhl, H.; Naydowski, C.; Danowski, F.; Bellenbeum, M.; Benn, R. Chem. Ber. 1984, 117, 3231-3254.
131. Reetz, M. T.; Westermann, J.; Steinbach, R.; Wenderoth, B.; Roland, P. Chem. Ber. 1985, 118, 1421-1440.
132. Yin, J. G.; Jones, W. M. Organometallics 1993, 12, 2013-2014.
133. Reamey, R. H.; Whitesides, G. M. J. Am. Chem. Soc. 1984, 106, 81-85.
134. Wenzel, T. T.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 4856-4867.
135. Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7332-7346.
136. McGhee, W. D.; Bergman, R. G. J. Am. Chem. Soc. 1988, 110, 4246-4262.
137. Fendrick, C. M.; Marks, T. J. J. Am. Chem. Soc. 1986, 108, 425-437.
138. Bergman, R. G.; Seidler, P. F.; Wenzel, T. T. J. Am. Chem. Soc. 1985, 107, 4358-4359.
139. Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1984, 106, 7272-7273.
140. Elschenbroich, A. S. Organometallics, A Concise Introduction, 2nd ed.; VCH: New York, 1992; p 244.
141. See ref 21, p 362.
142. For a recent leading reference to β-alkyl elimination, see: McNeill, K.; Andersen, R. A.; Bergman, R. G. J. Am. Ckem. Soc. 1997, 119, 11244-11254.
143. 145
144. Philips, R. L.; Puddephatt, R. J. J. Chem. Soc., Dalton Trans. 1978, 1732-1735.
145. Lehmkuhl, H.; Naydowski, C.; Danowski, F.; Bellenbaum, M.; Benn, R.; Rufinska, A.; Schroth, G.; Mynott, R.; von Stanislaw Pasynkiewicz, M. Chem. Ber. 1984, 117, 3231-3254.
146. For examples of strained organic molecules that are stabilized by coordination to transition-metal fragments, see refs 147-152.
147. Lee, G. A.; Lin, Y. H.; Huang, A. N.; Li, Y. C.; Jann, Y. C.; Chen, C. S. J. Am. Chem. Soc. 1999, 121, 5328-5329.
148. Wijsman, G. W.; Dewolf, W. H.; Bickelhaupt, F.; Kooijman, H.; Spek, A. L. J. Am. Chem. Soc. 1992, 114, 9191-9192.
149. Warner, P. M. Chem. Rev. 1989, 89, 1067-1093.
150. Borden, W. T. Chem. Rev. 1989, 89, 1095-1109.
151. Bly, R. S.; Hossain, M. M.; Lebioda, L. J. Am. Chem. Soc. 1985, 107, 5549-5550.
152. Godleski, S. A.; Gundlach, K. B.; Valpey, R. S. Organometallics 1985, 4, 296-302.
153. See ref 21, pp 356-376.
154. Cavell, K. J. Coord. Chem. Rev. 1996, 155, 209-243.
155. Blomberg, M. R. A.; Karlsson, C. A. M.; Siegbahn, P. E. M. J. Phys. Chem. 1993, 97, 9341-9350.
156. Alaimo, P. J.; Peters, D. W.; Arnold, J.; Bergman, R. G. J. Chem. Educ., in press.
157. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: New York, 1988; p 66.
158. Brookhart, M.; Grant, B.; Volpe, A. F., Jr. Organometallics 1992, 11, 3920-3922.
159. Woerpel, K. A.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 7888-7889.
160. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
161. Kar, A. K.; Lightner, D A. J. Heterocycl. Chem. 1998, 35, 795-804.
162. Olah, G. A.; Wang, Q. Synthesis 1992, 1090-1092.
163. SAINT: SAX Area-Detector Integration Program; Version 4.024; Siemens Industrial Automation, Inc., Madison, WI, 1995.
164. For references providing details of the crystallography techniques, see: Alaimo, P. J.; Bergman, R. G. Organometallics 1999, 18, 2707-2717.