Constrained geometry organoactinides as versatile catalysts for the intramolecular hydroamination/cyclization of primary and secondary amines having diverse tethered C-C unsaturation

Journal of the American Chemical Society

Volumn 129, Issue 14, 2007, Pages 4253-4271

  Stubbert, Bryan D ^a   Marks, Tobin J ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSTS; COMPLEXATION; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLVENTS;

INTRAMOLECULAR HYDROAMINATION; PROTODEAMINATION; SECONDARY AMINES;

ACTINIDES;

ACTINIDE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; AMINE; CHLORIDE; IODIDE; SILICON DERIVATIVE; SOLVENT;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; COMPLEX FORMATION; CYCLIZATION; DIASTEREOISOMER; HYDROAMINATION; NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; STEREOCHEMISTRY; X RAY DIFFRACTION;

ACTINOID SERIES ELEMENTS; ALKADIENES; ALKENES; AMINATION; AMINES; CARBON; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; HYDROGEN; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITROGEN;

EID: 34247098477     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0665444     Document Type: Article

References (179)

1. For general C-N bond-formation references, see: (a) Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368-3398.
2. (b) Hartwig, J. F. Science 2002, 297, 1653-1654.
3. (c) Beller, M.; Riermeier, T. H. In Transition Metals for Organic Synthesis, 1998, 1, 184-194.
4. (d) Hegedus, L. S. Angew. Chem., Int. Ed. 1988, 27, 1113-1126.
5. For general hydroamination reviews, see: (a) Odom, A. L. Dalton Trans. 2005, 225-233.
6. (b) Hultzsch, K. C. Adv. Synth. Catal. 2005, 347, 367-391.
7. (c) Hultzsch, K. C.; Gribkov, D. V.; Hampel, F. J. Organomet. Chem. 2005, 690, 4441-4452.
8. (d) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673-686.
9. (e) Doye, S. Synlett 2004, 1653-1672.
10. (f) Beller, M.; Tillack, A.; Seayad, J. In Transition Metals for Organic Synthesis, 2nd ed.; Beller, M., Bohm, C., Eds.; Wiley-VCH: Weinheim, 2004; pp 91-94.
11. (g) Roesky, P. W.; Mueller, T. E. Angew. Chem., Int. Ed. 2003, 42, 2708-2710.
12. (h) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104-114.
13. (i) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 2003, 935-946.
14. (j) Seayad, J.; Tillack, A.; Hartung, C. G.; Beller, M. Adv. Synth. Catal. 2002, 344, 795-813.
15. (k) Togni, A. In Catalytic Heterofunctionalization, 1st ed.; Togni, A., Gruetzmacher, H., Eds.; Wiley-VCH: New York, 2001; pp 91-141.
16. (l) Nobis, M.; Driessen-Holscher, B. Angew. Chem., Int. Ed. 2001, 40, 3983-3985.
17. (m) Eisen, M. S.; Straub, T.; Haskel, A. J. Alloys Compd. 1998, 271-273, 116-122.
18. (n) Mueller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703.
19. (a) Seyam, A. M.; Stubbert, B. D.; Jensen, T. R.; O'Donnell, J. J., III; Stern, C. L.; Marks, T. J. Inorg. Chim. Acta 2004, 357, 4029-4035.
20. (b) Ryu, J.-S.; Marks, T. J.; McDonald, F. E. J. Org. Chem. 2004, 69, 1038-1052.
21. (c) Hong, S.; Kawaoka, A. M.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 15878-15892.
22. (d) Hong, S.; Tian, S.; Metz, M. V.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 14768-14783.
23. (e) Ryu, J.-S.; Li, G. Y.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 12584-12605.
24. (f) Hong, S.; Marks, T. J. J. Am. Chem. Soc. 2002, 124, 7886-7887.
25. (g) Ryu, J.-S.; Marks, T. J.; McDonald, F. E. Org. Lett. 2001, 3, 3091-3094.
26. (h) Arredondo, V. M.; Tian, S.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1999, 121, 3633-3639.
27. (i) Arredondo, V. M.; McDonald, F. E.; Marks, T. J. Organometallics 1999, 18, 1949-1960.
28. (j) Tian, S.; Arredondo, V. M.; Stern, C. L.; Marks, T. J. Organometallics 1999, 18, 2568-2570.
29. (k) Arredondo, V. M.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 4871-4872.
30. (l) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 1757-1771.
31. (m) Roesky, P. W.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4705-4711.
32. (n) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295-9306.
33. (o) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770-3772.
34. (p) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707-708.
35. (q) Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagne, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241-10254.
36. (r) Giardello, M. A.; Conticello, V. P.; Brard, L.; Sabat, M.; Rheingold, A. L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10212-10240.
37. (s) Li, Y.; Fu, P.-F.; Marks, T. J. Organometallics 1994, 13, 439-440.
38. (t) Gagne, M. R.; Brard, L.; Conticello, V. P.; Giardello, M. A.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 2003-2005.
39. (u) Gagne, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275-294.
40. (v) Gagne, M. R.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 4108-4109.
41. For additional examples of group 3- and lanthanide-catalyzed HA, see: (a) Bambina, S.; Tsurugi, H.; van Leusen, D.; Hessen, B. Dalton Trans. 2006, 1157-1161.
42. (b) Gribkov, D. V.; Hultzsch, K. C.; Hampel, F. J. Am. Chem. Soc. 2006, 128, 3748-3759.
43. (c) Panda, T. K.; Zulys, A.; Gamer, M. T.; Roesky, P. W. Organometallics 2005, 24, 2197-2202.
44. (d) Collin, J.; Daran, J.-C.; Jacquet, O.; Schulz, E.; Trifonov, A. Chem. Eur. J. 2005, 11, 3455-3462.
45. (e) Kim, J. Y.; Livinghouse, T. Org. Lett. 2005, 7, 4391-4393.
46. (f) Kim, J. Y.; Livinghouse, T. Org. Lett. 2005, 7, 1737-1739.
47. (g) Molander, G. A.; Hasegawa, H. Heterocycles 2004, 64, 467-474.
48. (h) Lauterwasser, F.; Hayes, P. G.; Brase, S.; Piers, W. E.; Schafer, L. L. Organometallics 2004, 23, 2234-2237.
49. (i) Hultzsch, K. C.; Hampel, F.; Wagner, T. Organometallics 2004, 23, 2601-2612.
50. (j) O'Shaughnessy, P. N.; Gillespie, K. M.; Knight, P. D.; Munslow, I. J.; Scott, P. Dalton Trans. 2004, 2251-2256.
51. (k) O'Shaughnessy, P. N.; Scott, P. Tetrahedron: Asymmetry 2003, 14, 1979-1983.
52. (l) O'Shaughnessy, P. N.; Knight, P. D.; Morton, C.; Gillespie, K. M.; Scott, P. Chem. Commun. 2003 1770-1771.
53. (m) Kim, Y. K.; Livinghouse, T.; Horino, Y. J. Am. Chem. Soc. 2003, 125, 9560-9561.
54. (n) Molander, G. A.; Pack, S. K. Tetrahedron 2003, 59, 10581-10591.
55. (o) Molander, G. A.; Pack, S. K. J. Org. Chem. 2003, 68, 9214-9220.
56. (p) Kim, Y. K.; Livinghouse, T. Angew. Chem., Int. Ed. 2002, 41, 3645-3647.
57. (q) Bürgstein, M. R.; Berberich, H.; Roesky, P. W. Chem. Eur. J. 2001, 7, 3078-3085.
58. (r) Kim, Y. K.; Livinghouse, T.; Bercaw, J. E. Tetrahedron Lett. 2001, 42, 2933-2935.
59. (s) Molander, G. A.; Dowdy, E. D. J. Org. Chem. 1999, 64, 6515-6517.
60. (t) Molander, G. A.; Dowdy, E. D. J. Org. Chem. 1998, 63, 8983-8988.
61. For group 4 catalysts see: (a) Thomson, R. K.; Bexrud, J. A.; Schafer, L. L. Organometallics 2006, 25, 4069-4071.
62. (b) Lee, A. V.; Schafer, L. L. Organometallics 2006, 25, 5249-5254.
63. (c) Esteruelas, M. A.; Lopez, A. M.; Mateo, A. C.; Onate, E. Organometallics 2006, 25, 1448-1460.
64. (d) Bexrud, J. A.; Beard, J. D.; Leitch, D. C.; Schafer, L. L. Org. Lett. 2005, 7, 1959-1962.
65. (e) Esteruelas, M. A.; Lopez, A. M.; Mateo, A. C.; Onate, E. Organometallics 2005, 24, 5084-5094.
66. (f) Kim, H.; Lee, P. H.; Livinghouse, T. Chem. Commun. 2005, 5205-5207.
67. (g) Hoover, J. M.; Petersen, J. R.; Pikul, J. H.; Johnson, A. R. Organometallics 2004, 23, 4614-4620.
68. (h) Gribkov, D. V.; Hultzsch, K. C. Angew. Chem., Int. Ed. 2004, 43, 5542-5546.
69. (i) Knight, P. D.; Munslow, I.; O'Shaughnessy, P. N.; Scott, P. Chem. Commun. 2004, 894-895.
70. (j) Li, C.; Thompson, R. K.; Gillon, B.; Patrick, B. O.; Schafer, L. L. Chem. Commun. 2003, 2462-2463.
71. (k) Ackermann, L.; Bergman, R. G. Org. Lett. 2002, 4, 1475-1478.
72. (l) Ackermann, L.; Bergman, R. G.; Loy, R. N. J. Am. Chem. Soc. 2003, 125, 11956-11963.
73. See for example: (a) Krogstad, D. A.; Cho, J.; DeBoer, A. J.; Klitzke, J. A.; Sanow, W. R.; Williams, H. A.; Halfen, J. A. Inorg. Chim. Acta 2006, 359, 136-148.
74. (b) Zhang, J.; Yang, C.-G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798-1799.
75. (c) Kadzimirsz, D.; Hildebrandt, D.; Merz, K.; Dyker, G. Chem. Commun. 2006, 661-662.
76. (d) Bajracharya, G. B.; Huo, Z.; Yamamoto, Y. J. Org. Chem. 2005, 70, 4883-4886.
77. (e) Field, L. D.; Messerle, B. A.; Vuong, K. Q.; Turner, P. Organometallics 2005, 24, 4241-4250.
78. (f) Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2005, 127, 1070-1071.
79. (g) Zulys, A.; Dochnahl, M.; Hollmann, D.; Löhnwitz, K.; Herrmann, J.-S.; Roesky, P. W.; Blechert, S. Angew. Chem. Int. Ed. 2005, 44, 7794-7798.
80. (h) Lutete, L. M.; Kadota, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 1622-1623.
81. (i) Schlummer, B.; Hartwig, J. F. Org. Lett. 2002, 4, 1471-1474.
82. Crimmin, M. R.; Casely, I. J.; Hill, M. S. J. Am. Chem. Soc. 2005, 127, 2042-2043.
83. (a) Kadzimirsz, D.; Hildebrandt, D.; Merz, K.; Dyker, G. Chem. Commun. 2006, 661-662.
84. (b) Zhang, J.; Yang, C.-G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798-1799.
85. (c) Muller, T. E.; Grosche, M.; Herdtweck, E.; Pleier, A.-K.; Walter, E.; Yan, Y.-K. Organometallics 2000, 19, 170-183.
86. For reviews of enantioselective catalysis with lanthanides, see: (a) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850.
87. (b) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2225.
88. (c) Molander, G. A. Pure Appl. Chem. 2000, 72, 1757-1761.
89. Shannon, R. D. Acta Crystallogr. 1976, A32, 751-67.
90. For reviews of constrained geometry catalysts, see: (a) Gromada, J.; Carpentier, J.-F.; Mortreux, A. Coord. Chem. Rev. 2004, 248, 397-410.
91. (b) Okuda, J. Dalton Trans. 2003, 2367-2378.
92. (c) Arndt, S.; Okuda, J. Chem. Rev. 2002, 102, 1953-1976.
93. (d) Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. Angew. Chem., Int. Ed. 1999, 38, 428-447.
94. For reviews of 4f- and 5f-element chemistry, see: (a) Burns, C. J.; Neu, M. P.; Boukhalfa, H.; Gutowski, K. E.; Bridges, N. J.; Rogers, R. D. In Comprehensive Coordination Chemistry II, 1st ed.; McCleverty, J. A., Meyer, T. J., Eds.; Elsevier Pergamon: Amsterdam, 2004; Vol. 3, pp 189-345.
95. (b) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102, 1851-1896.
96. (c) Molander, G. A.; Dowdy, E. D. Top. Organomet. Chem. 1999, 2, 119-154.
97. (d) Edelmann, F. T. Angew. Chem., Int. Ed. 1995, 34, 2466-88.
98. (e) Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 4, pp 11-213.
99. (f) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362.
100. (g) Molander, G. A. Chem. Rev. 1992, 92, 29-68.
101. (h) The Chemistry of the Actinide Elements; Katz, J. J., Seaborg, G. T., Morss, L. R., Eds.; Chapman and Hall: New York, 1986.
102. (i) Fundamental and Technological Aspects of Organo-f-Element Chemistry; Marks, T. J., Fragalà, I. L., Eds.; Reidel: Dordrecht, 1985.
103. (j) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1982; Vol. 3, pp 173-270.
104. (k) Marks, T. J. Chemistry and Spectroscopy of f Element Organometallics, Part II. The Actinides. Progress in Inorganic Chemistry 1979, 25, 224.
105. (l) Marks, T. J. Chemistry and Spectroscopy of f Element Organometallics, Part I. The Lanthanides. Progress in Inorganic Chemistry 1978, 24, 51.
106. (a) Cotton, F. A.; Wilkinson, C.; Murillo, C. A.; Bochmann, M. Advanced Inorganic Chemistry, 6th ed.; John Wiley & Sons, Inc.: New York, 1999.
107. (b) Kettle, S. F. A. Physical Inorganic Chemistry: A Coordination Chemistry Approach; Oxford University Press: New York, 1998.
108. (c) Huheey, J. E.; Keiter, E. A.; Keiter, R. L. Inorganic Chemistry; Principles of Structure and Reactivity, 4th ed.; HarperCollins College Publishers: New York, 1993.
109. See, for example: (a) Barnea, E.; Eisen, M. S. Coord. Chem. Rev. 2006, 250, 855-899.
110. (b) Burns, C. J. Science 2005, 309, 1823-1824.
111. (c) Evans, W. J.; Kozimor, S. A.; Ziller, J. W. Science 2005, 309, 1835-1838.
112. (d) Castro-Rodriguez, I.; Meyer, K. J. Am. Chem. Soc. 2005, 127, 11242-11243.
113. (e) Evans, W. J.; Kozimor, S. A.; Ziller, J. W.; Kaltsoyannis, N. J. Am. Chem. Soc. 2004, 126, 14533-14547.
114. (f) Castro-Rodriguez, I.; Nakai, H.; Zakharov, L. N.; Rheingold, A. L.; Meyer, K. Science 2004, 305, 1757-1760.
115. (g) Castro-Rodriguez, I.; Nakai, H.; Gantzel, P.; Zakharov, L. N.; Rheingold, A. L.; Meyer, K. J. Am. Chem. Soc. 2003, 125, 15734-15735.
116. (h) Diaconescu, P. L.; Arnold, P. L.; Baker, T. A.; Mindiola, D. J.; Cummins, C. C. J. Am. Chem. Soc. 2000, 122, 6108-6109.
117. Stubbert, B. D.; Stern, C. L.; Marks, T. J. Organometallics 2003, 22, 4836-4838.
118. Stubbert, B. D.; Marks, T. J. J. Am. Chem. Soc 2007, 129, in press.
119. Jamerson, J. D. Ph.D. Thesis, University of Alberta, 1974.
120. Gillespie, R. D.; Burwell, R. L., Jr.; Marks, T. J. Langmuir 1990, 6, 1465-1477.
121. 2 are dimeric (or trimeric) species. See Supporting Information for experimental details.
122. Espenson, J. H. Chemical Kinetics and Reaction Mechanisms, 2nd ed.; McGraw-Hill, Inc.: New York, 1995.
123. (a) Berthet, J. C.; Ephritikhine, M. Coord. Chem. Rev. 1998, 178-180, 83-116.
124. (b) Kuhlman, R. Coord. Chem. Rev. 1997, 167, 205-232.
125. (c) Bradley, D. C.; Chisholm, M. H. Acc. Chem. Res. 1976, 9, 273-280.
126. (a) Bagnall, K. W.; Yanir, E. J. Inorg. Nucl. Chem. 1974, 36, 777-779,
127. (b) Watt, G. W.; Gadd, K. F. Inorg. Nucl. Chem. Lett. 1973, 9, 203-205.
128. (a) Ossola, F.; Rossetto, G.; Zanella, P.; Arudini, A.; Jamerson, J. D.; Takats, J.; Dormond, A. Inorg. Synth. 1992, 29, 234-238.
129. (b) Arduini, A. L.; Takats, J. Inorg. Chem. 1981, 20, 2480-2485.
130. (e) Arduini, A. L.; Jamerson, J. D.; Takats, J. Inorg. Chem. 1981, 20, 2474-2479.
131. (d) Arduini, A. L.; Edelstein, M.; Jamerson, J. D.; Reynolds, J. G.; Schimd, K.; Takats, J. lnorg. Chem. 1981, 20, 2470-2474.
132. (e) Jamerson, J. D.; Takats, J. J. Organomet. Chem. 1974, 78, C23-C25.
133. (f) Jones, R. G.; Karmas, G.; Martin, G. A., Jr.; Gilman, H. J. Am. Chem. Soc. 1956, 78, 4285-4286.
134. (a) Taft, R. W.; Bordwell, F. G. Acc. Chem. Res. 1988, 21, 463-469.
135. (b) Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463.
136. (c) Bordwell, F. G.; Bausch, M. J. J. Am. Chem. Soc. 1983, 105, 6188-6189.
137. (a) Trnka, T. M.; Bonanno, J. B.; Bridgewater, B. M.; Parkin, G. Organometallics 2001, 20, 3255-3264.
138. (b) Roussel, P.; Alcock, N. W.; Boaretto, R.; Kingsley, A. J.; Munslow, I. J.; Sanders, C. J.; Scott, P. Inorg. Chem. 1999, 38, 3651-3656.
139. (c) Straub, T.; Frank, W.; Reiss, G. J.; Eisen, M. S. Dalton Trans. 1996, 2541-2546.
140. (d) Scott, P.; Hitchcock, P. B. Dalton Trans. 1995, 603-609.
141. (e) Gilbert, T. M.; Ryan, R. R.; Sattelberger, A. P. Organometallics 1988, 7, 2514-2518.
142. (a) Brinkman, E. A.; Berger, S.; Brauman, J. I. J. Am. Chem. Soc. 1994, 116, 8304-8310.
143. (b) Hopkinson, A. C.; Lien, M. H. J. Org. Chem. 1981, 46, 998-1003.
144. See, for example: Basolo, F. New J. Chem. 1994, 18, 19-24.
145. (a) Evans, W. J.; Kozimor, S. A.; Hillman, W. R.; Ziller, J. W. Organometallics 2005, 24, 4676-4683.
146. (b) Jantunen, K. C.; Burns, C. J.; Castro-Rodriguez, I.; Da Re, R. E.; Golden, J. T.; Morris, D. E.; Scott, B. L.; Taw, F. L.; Kiplinger, J. L. Organometallics 2004, 23, 4682-4692.
147. (a) Fendrick, C. M.; Schertz, L. D.; Day, V. W.; Marks, T. J. Organometallics 1988, 7, 1828-1838.
148. (b) Fendrick, C. M.; Mintz, E. A.; Schertz, L. D.; Marks, T. J. Organometallics 1984, 3, 819-821.
149. Schnabel, R. C.; Scott, B. L.; Smith, W. H.; Burns, C. J. J. Organomet. Chem. 1999, 591, 14-23.
150. Carpenetti, D. W.; Kloppenburg, L.; Kupec, J. T.; Petersen, J. L. Organometallics 1996, 15, 1572-1581.
151. See, for example: Fagan, P. J.; Manriquez, J. M.; Marks, T. J.; Day, C. S.; Vollmer, S. H.; Day, V. W. Organometallics 1982, 1, 170-180 and references therein.
152. Golden, J. T.; Kazul'kin, D. N.; Scott, B. L.; Voskoboynikov, A. Z.; Burns, C. J. Organometallics 2003, 22, 3971-3973.
153. For general reviews, see: (a) Barron, A. R. Metallocene-Based Polyolefins 2000, 1, 33-67.
154. (b) Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391-1434 and references therein.
155. 1 values at 25°C estimated on the basis of activation parameters determined in the lead reference.
156. 2 species (see refs 2a,h-n and 16 for details).
157. Stubbert, B. D. Ph.D. Thesis, Northwestern University, 2006. Prolonged reaction times and forcing conditions (T > 120°C) in alkane and aromatic solvents do not induce catalyst decomposition with similar 1° and 2° amine substrates.
158. Sammes, P. G.; Weller, D. J. Synthesis 1995, 1205-1222.
159. (a) Motta, A.; Fragala, I. L.; Marks, T. J. Organometallics 2006, 25, 5533-5539.
160. (b) Motta, A.; Lanza, G.; Fragala, I. L.; Marks, T. J. Organometallics 2004, 23, 4097-4104.
161. (a) Tobisch, S. Dalton Trans. 2006, No. 35, 4277-4285.
162. (b) Tobisch, S. Chem. Eur. J. 2006, 12, 2520-2531.
163. (c) Tobisch, S. J. Am. Chem. Soc. 2005, 127, 11979-11988.
164. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; John Wiley & Sons: New York, 1992.
165. See, for example: (a) Shakhnovich, E. I. Nat. Struct. Biol. 1999, 6, 99-102.
166. (b) Stryer, L. Biochemistry, 4th ed.; W. H. Freeman and Co.: New York, 1995; pp 181-206.
167. Hazari, N.; Mountford, P. Acc. Chem. Res. 2005, 38, 839-849.
168. (a) Walton, J. C.; Studer, A. Acc. Chem. Res. 2005, 38, 794-802.
169. (b) Kemper, J.; Studer, A. Angew. Chem., Int. Ed. 2005, 44, 4914-4917.
170. (c) Newcomb, M.; Burchill, M. T.; Deeb, T. M. J. Am. Chem. Soc. 1988, 110, 6528-6535.
171. insertion appears operative here).
172. (a) Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95-102.
173. (b) Mandolini, L. J. Am. Chem. Soc. 1978, 100, 550-554.
174. (a) Baranger, A. M.; Walsh, P. J.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 2753-2763.
175. (b) Walsh, P. J.; Baranger, A. M.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 1708-1719.
176. (a) Straub, T.; Haskel, A.; Neyroud, T. G.; Kapon, M.; Botoshansky, M.; Eisen, M. S. Organometallics 2001, 20, 5017-5035.
177. (b) Haskel, A.; Straub, T.; Eisen, M. S. Organometallics 1996, 15, 3773-3775.
178. 1.
179. Wang, J.; Dash, A. K.; Kapon, M.; Berthet, J.-C.; Ephritikhine, M.; Eisen, M. S. Chem. Eur. J. 2002, 8, 5384-5396.