Energetics and mechanism of organolanthanide-mediated aminoalkene hydroamination/cyclization. A density functional theory analysis

Organometallics

Volumn 23, Issue 17, 2004, Pages 4097-4104

  Motta, Alessandro ^a   Lanza, Giuseppe ^a   Fragalà, Ignazio L ^a   Marks, Tobin J ^b  

^a UNIVERSITY OF CATANIA   (Italy)

^b NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; APPROXIMATION THEORY; CATALYSTS; DATA REDUCTION; DISSOCIATION; ELECTROSTATICS; INFORMATION ANALYSIS; ISOMERS; OLEFINS; ORGANOMETALLICS; POLARIZATION; REACTION KINETICS; SOLVENTS; THERMODYNAMICS; TRANSITION METALS;

CYCLIZATION; DENSITY FUNCTIONAL THEORY; HYDROAMINATION; ORGANOLANTHENIDES;

RARE EARTH ELEMENTS;

EID: 84961975555     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049666i     Document Type: Article

References (111)

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4. For some leading review references, see: (a) Tsuji, J. Transition Metal Reagents and Catalysts. Innovations in Organic Synthesis; Wiley: New York, 2000. (b) Kobayashi, S., Ed. Lanthanides: Chemistry and Use in Organic Synthesis; Springer-Verlag: Berlin, 1999. (c) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: New York, 1994. (d) Hegedus, L. S., Ed. Comprehensive Organometallic Chemistry II. Transition Metal Reagents in Organic Synthesis; Pergamon: Oxford, 1995; Vol. 12. (e) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994. (f) Molander, G. A. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Ed.; John Wiley Ltd: London, 1989; Vol. 5, Chapter 8. (g) McMurry, J. E. Chem. Rev. 1989, 89, 1523-1524. (h) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. (i) Collman, J. P.; Hegedus, L. S.; Norton J. R.; Finke R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987; Part III. (j) Reez, M. T. Organo-lanthanum Reagents in Organic Synthesis; Spinger-Verlag: Berlin, 1986. (k) Kagan, H. B. In Fundamental and Technological Aspects of Organo-f-Elements Chemistry; Marks, T. J., Fragalà, I. L., Eds.; Reidel: Dordrecht, The Netherlands, 1985; Chapter 2.
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33. Ryu, J. S.; Marks, T. J.; McDonald, F. E. J. Org. Chem. 2004, 69, 1038-1052.
34. Hong, S.; Kawaoka, A. M.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 15878-15892.
35. (e) Ryu, J.-S.; Marks, T. J.; McDonald, F. E. J. Org. Chem. 2004, 69, 1038-1052.
36. (a) Beller, M.; Breindl, C.; Eichberger, M.; Hartung, C. G.; Seayad, J.; Thiel, O. R.; Tillack, A.; Trauthwein, H. Synlett 2002, 10, 1579-1594, and references therein.
37. (b) Pawlas, J.; Nakao, Y.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 3669-3679.
38. Hong, S.; Marks, T. J. J. Am. Chem. Soc. 2002, 124, 7886.
39. Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366-4367.
40. (e) Minami, T.; Okamoto, H.; Ikeda, S.; Tanaka, R.; Ozawa, F.; Yoshifuji, M. Angew. Chem., Int. Ed. 2001, 40, 4501-4503.
41. (f) Nettekoven, U.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 1166-1167.
42. (g) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 9546-9547.
43. (h) Beller, M.; Thiel, O. R.; Trauthwein, H.; Hartung, C. G. Chem. Eur. J. 2000, 6, 2513-2522.
44. Bozel, J. J.; Hegedus, L. S. J. Org. Chem. 1981, 46, 2561-2563.
45. Kawatsura, M.; Hartwig, J. F. Organometallics 2001, 20, 1960-1964.
46. Fadini, L.; Togni, A. Chem. Commun. 2003, 30-31.
47. (a) 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.
48. (b) Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241-10254.
49. (c) Gagné M. R.; Brard, L.; Conticello, V. P.; Giardello, M. A.; Stern, C. L.; Marks, T. J. Organometallics 1992, 11, 2003-2005.
50. (d) Douglass, M. R.; Ogasawara, M.; Hong, S.; Metz, M. V.; Marks, T. J. Organometallics 2002, 21, 283-292.
51. (e) Hong, S.; Tian, S.; Metz, M. V.; Marks, T. J. J. Am. Chem. Soc., 2003, 125, 14768-14783.
52. (f) Hong, S.; Marks, T. J. Accts. Chem. Res., published online Jun. 29, 2004 http://dx.doi.org/10.1021/ar040051r.
53. (a) Dorta, R.; Egli, P.; Zürcher, F.; Togni, A. J. Am. Chem. Soc. 1997, 119, 10857-10858.
54. (b) Bieler, N.; Egli, P.; Dorta, R.; Togni, A.; Eyer, M. (Lonza A.G.) EP 0 909 762A2, 1999 [Chem. Abstr. 1999, 130, 305622].
55. (b) Bieler, N.; Egli, P.; Dorta, R.; Togni, A.; Eyer, M. (Lonza A.G.) EP 0 909 762A2, 1999 [Chem. Abstr. 1999, 130, 305622].
56. (a) Casalnuovo, A. L.; Calabrese, J. C.; Milsein, D. J. Am. Chem. Soc. 1988, 110, 6738-6744.
57. (b) Aizenberg, M.; Milstein, D.; Tulip, T. H. Organometallics 1996, 15, 4093-4095.
58. Hydrogenation: (a) Obora, Y.; Otha, T.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1997, 119, 3745-3755. (b) Roesky, P. W.; Denninger, U.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4486-4492. (c) Haar, C M.; Sern, C. L.; Marks, T. J. Organometallics 1996, 15, 1765-1784.
59. Hydrogenation: (a) Obora, Y.; Otha, T.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1997, 119, 3745-3755. (b) Roesky, P. W.; Denninger, U.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4486-4492. (c) Haar, C M.; Sern, C. L.; Marks, T. J. Organometallics 1996, 15, 1765-1784.
60. Hydrogenation: (a) Obora, Y.; Otha, T.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1997, 119, 3745-3755. (b) Roesky, P. W.; Denninger, U.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 4486-4492. (c) Haar, C M.; Sern, C. L.; Marks, T. J. Organometallics 1996, 15, 1765-1784.
61. Hydrosilylation: (a) Molander, G. A.; Corrette, C. P. Organometallics 1998, 17, 5504-5512. (b) Schumann, H.; Keitsch, M. R.; Winterfeld, J.; Muhle, S.; Molander, G. A. J. Organomet. Chem. 1998, 559, 181-190. (c) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157-7168. (d) Molander, G. A.; Julius, M. J. Org. Chem. 1992, 57, 6347-6351. (e) Sakakura, T.; Lautenschlager, H.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1991, 40-41.
62. Hydrosilylation: (a) Molander, G. A.; Corrette, C. P. Organometallics 1998, 17, 5504-5512. (b) Schumann, H.; Keitsch, M. R.; Winterfeld, J.; Muhle, S.; Molander, G. A. J. Organomet. Chem. 1998, 559, 181-190. (c) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157-7168. (d) Molander, G. A.; Julius, M. J. Org. Chem. 1992, 57, 6347-6351. (e) Sakakura, T.; Lautenschlager, H.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1991, 40-41.
63. Hydrosilylation: (a) Molander, G. A.; Corrette, C. P. Organometallics 1998, 17, 5504-5512. (b) Schumann, H.; Keitsch, M. R.; Winterfeld, J.; Muhle, S.; Molander, G. A. J. Organomet. Chem. 1998, 559, 181-190. (c) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157-7168. (d) Molander, G. A.; Julius, M. J. Org. Chem. 1992, 57, 6347-6351. (e) Sakakura, T.; Lautenschlager, H.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1991, 40-41.
64. Hydrosilylation: (a) Molander, G. A.; Corrette, C. P. Organometallics 1998, 17, 5504-5512. (b) Schumann, H.; Keitsch, M. R.; Winterfeld, J.; Muhle, S.; Molander, G. A. J. Organomet. Chem. 1998, 559, 181-190. (c) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157-7168. (d) Molander, G. A.; Julius, M. J. Org. Chem. 1992, 57, 6347-6351. (e) Sakakura, T.; Lautenschlager, H.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1991, 40-41.
65. Hydrosilylation: (a) Molander, G. A.; Corrette, C. P. Organometallics 1998, 17, 5504-5512. (b) Schumann, H.; Keitsch, M. R.; Winterfeld, J.; Muhle, S.; Molander, G. A. J. Organomet. Chem. 1998, 559, 181-190. (c) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157-7168. (d) Molander, G. A.; Julius, M. J. Org. Chem. 1992, 57, 6347-6351. (e) Sakakura, T.; Lautenschlager, H.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1991, 40-41.
66. Hydroboration: (a) Molander, G. A.; Pfeiffer, D. Org. Lett. 2001, 3, 361-363. (b) Bijpost, E. A.; Duchateau, R.; Teuben, J. H. J. Mol. Catal. 1995, 95, 121-128. (c) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220-9221.
67. Hydroboration: (a) Molander, G. A.; Pfeiffer, D. Org. Lett. 2001, 3, 361-363. (b) Bijpost, E. A.; Duchateau, R.; Teuben, J. H. J. Mol. Catal. 1995, 95, 121-128. (c) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220-9221.
68. Hydroboration: (a) Molander, G. A.; Pfeiffer, D. Org. Lett. 2001, 3, 361-363. (b) Bijpost, E. A.; Duchateau, R.; Teuben, J. H. J. Mol. Catal. 1995, 95, 121-128. (c) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220-9221.
69. Hydrophosphination: (a) Douglaas, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824-1825. (b) Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221-10238. (c) Kawaoka, A. M.; Douglass, M. R.; Marks, T. J. Organometallics 2003, 22, 4030-4032.
70. Hydrophosphination: (a) Douglaas, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824-1825. (b) Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221-10238. (c) Kawaoka, A. M.; Douglass, M. R.; Marks, T. J. Organometallics 2003, 22, 4030-4032.
71. Hydrophosphination: (a) Douglaas, M. R.; Marks, T. J. J. Am. Chem. Soc. 2000, 122, 1824-1825. (b) Douglass, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 10221-10238. (c) Kawaoka, A. M.; Douglass, M. R.; Marks, T. J. Organometallics 2003, 22, 4030-4032.
72. For recent organolanthanide reviews, see: (a) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850. (b) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102, 1851-1896, (c) Arndt, S.; Okuda, J. Chem. Rev. 2002, 102, 1953-1976. (d) Molander, G. A.; Romero, A. C. Chem. Rev. 2002, 102, 2161-2186. (e) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210. (f) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2226. (g) Molander, G. A. Chemtracts: Org. Chem. 1998, 18, 237-263. (h) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247-276. (i) Edelmann, F. T. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2. (j) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865-986. (k) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362. (l) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131-177. (m) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21.
73. For recent organolanthanide reviews, see: (a) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850. (b) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102, 1851-1896, (c) Arndt, S.; Okuda, J. Chem. Rev. 2002, 102, 1953-1976. (d) Molander, G. A.; Romero, A. C. Chem. Rev. 2002, 102, 2161-2186. (e) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210. (f) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2226. (g) Molander, G. A. Chemtracts: Org. Chem. 1998, 18, 237-263. (h) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247-276. (i) Edelmann, F. T. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2. (j) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865-986. (k) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362. (l) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131-177. (m) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21.
74. For recent organolanthanide reviews, see: (a) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850. (b) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102, 1851-1896, (c) Arndt, S.; Okuda, J. Chem. Rev. 2002, 102, 1953-1976. (d) Molander, G. A.; Romero, A. C. Chem. Rev. 2002, 102, 2161-2186. (e) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210. (f) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2226. (g) Molander, G. A. Chemtracts: Org. Chem. 1998, 18, 237-263. (h) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247-276. (i) Edelmann, F. T. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2. (j) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865-986. (k) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362. (l) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131-177. (m) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21.
75. For recent organolanthanide reviews, see: (a) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850. (b) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102, 1851-1896, (c) Arndt, S.; Okuda, J. Chem. Rev. 2002, 102, 1953-1976. (d) Molander, G. A.; Romero, A. C. Chem. Rev. 2002, 102, 2161-2186. (e) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210. (f) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2226. (g) Molander, G. A. Chemtracts: Org. Chem. 1998, 18, 237-263. (h) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247-276. (i) Edelmann, F. T. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2. (j) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865-986. (k) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362. (l) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131-177. (m) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21.
76. For recent organolanthanide reviews, see: (a) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850. (b) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102, 1851-1896, (c) Arndt, S.; Okuda, J. Chem. Rev. 2002, 102, 1953-1976. (d) Molander, G. A.; Romero, A. C. Chem. Rev. 2002, 102, 2161-2186. (e) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210. (f) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2226. (g) Molander, G. A. Chemtracts: Org. Chem. 1998, 18, 237-263. (h) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247-276. (i) Edelmann, F. T. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2. (j) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865-986. (k) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362. (l) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131-177. (m) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21.
77. For recent organolanthanide reviews, see: (a) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850. (b) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102, 1851-1896, (c) Arndt, S.; Okuda, J. Chem. Rev. 2002, 102, 1953-1976. (d) Molander, G. A.; Romero, A. C. Chem. Rev. 2002, 102, 2161-2186. (e) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210. (f) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2226. (g) Molander, G. A. Chemtracts: Org. Chem. 1998, 18, 237-263. (h) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247-276. (i) Edelmann, F. T. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2. (j) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865-986. (k) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362. (l) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131-177. (m) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21.
78. For recent organolanthanide reviews, see: (a) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850. (b) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102, 1851-1896, (c) Arndt, S.; Okuda, J. Chem. Rev. 2002, 102, 1953-1976. (d) Molander, G. A.; Romero, A. C. Chem. Rev. 2002, 102, 2161-2186. (e) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210. (f) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2226. (g) Molander, G. A. Chemtracts: Org. Chem. 1998, 18, 237-263. (h) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247-276. (i) Edelmann, F. T. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2. (j) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865-986. (k) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362. (l) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131-177. (m) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21.
79. For recent organolanthanide reviews, see: (a) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850. (b) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102, 1851-1896, (c) Arndt, S.; Okuda, J. Chem. Rev. 2002, 102, 1953-1976. (d) Molander, G. A.; Romero, A. C. Chem. Rev. 2002, 102, 2161-2186. (e) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210. (f) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2226. (g) Molander, G. A. Chemtracts: Org. Chem. 1998, 18, 237-263. (h) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247-276. (i) Edelmann, F. T. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2. (j) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865-986. (k) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362. (l) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131-177. (m) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21.
80. For recent organolanthanide reviews, see: (a) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850. (b) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102, 1851-1896, (c) Arndt, S.; Okuda, J. Chem. Rev. 2002, 102, 1953-1976. (d) Molander, G. A.; Romero, A. C. Chem. Rev. 2002, 102, 2161-2186. (e) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210. (f) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2226. (g) Molander, G. A. Chemtracts: Org. Chem. 1998, 18, 237-263. (h) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247-276. (i) Edelmann, F. T. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2. (j) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865-986. (k) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362. (l) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131-177. (m) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21.
81. For recent organolanthanide reviews, see: (a) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850. (b) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102, 1851-1896, (c) Arndt, S.; Okuda, J. Chem. Rev. 2002, 102, 1953-1976. (d) Molander, G. A.; Romero, A. C. Chem. Rev. 2002, 102, 2161-2186. (e) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210. (f) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2226. (g) Molander, G. A. Chemtracts: Org. Chem. 1998, 18, 237-263. (h) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247-276. (i) Edelmann, F. T. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2. (j) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865-986. (k) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362. (l) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131-177. (m) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21.
82. For recent organolanthanide reviews, see: (a) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850. (b) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102, 1851-1896, (c) Arndt, S.; Okuda, J. Chem. Rev. 2002, 102, 1953-1976. (d) Molander, G. A.; Romero, A. C. Chem. Rev. 2002, 102, 2161-2186. (e) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210. (f) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2226. (g) Molander, G. A. Chemtracts: Org. Chem. 1998, 18, 237-263. (h) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247-276. (i) Edelmann, F. T. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2. (j) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865-986. (k) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362. (l) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131-177. (m) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21.
83. For recent organolanthanide reviews, see: (a) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850. (b) Edelmann, F. T.; Freckmann, D. M. M.; Schumann, H. Chem. Rev. 2002, 102, 1851-1896, (c) Arndt, S.; Okuda, J. Chem. Rev. 2002, 102, 1953-1976. (d) Molander, G. A.; Romero, A. C. Chem. Rev. 2002, 102, 2161-2186. (e) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210. (f) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211-2226. (g) Molander, G. A. Chemtracts: Org. Chem. 1998, 18, 237-263. (h) Edelmann, F. T. Top. Curr. Chem. 1996, 179, 247-276. (i) Edelmann, F. T. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2. (j) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865-986. (k) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283-362. (l) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131-177. (m) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21.
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109. Metal-ligand bond enthalpies from: (a) Nolan, S. P.; Stern, D.; Hedden, D.; Marks, T. J. ACS Symp. Ser. 1990, 428, 159-174. (b) Nolan, S. P.; Stern, D.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 7844-7853. (c) Schock, L. E.; Marks, T. J. J. Am. Chem. Soc. 1988, 110, 7701-7715. (d) Bruno, J. W.; Marks, T. J.; Morss, L. R. J. Am. Chem. Soc. 1983, 105, 6824-6832.
110. Metal-ligand bond enthalpies from: (a) Nolan, S. P.; Stern, D.; Hedden, D.; Marks, T. J. ACS Symp. Ser. 1990, 428, 159-174. (b) Nolan, S. P.; Stern, D.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 7844-7853. (c) Schock, L. E.; Marks, T. J. J. Am. Chem. Soc. 1988, 110, 7701-7715. (d) Bruno, J. W.; Marks, T. J.; Morss, L. R. J. Am. Chem. Soc. 1983, 105, 6824-6832.
111. Metal-ligand bond enthalpies from: (a) Nolan, S. P.; Stern, D.; Hedden, D.; Marks, T. J. ACS Symp. Ser. 1990, 428, 159-174. (b) Nolan, S. P.; Stern, D.; Marks, T. J. J. Am. Chem. Soc. 1989, 111, 7844-7853. (c) Schock, L. E.; Marks, T. J. J. Am. Chem. Soc. 1988, 110, 7701-7715. (d) Bruno, J. W.; Marks, T. J.; Morss, L. R. J. Am. Chem. Soc. 1983, 105, 6824-6832.