Platinum-catalyzed acrylonitrile hydrophosphination. P-C bond formation via olefin insertion into a Pt-P bond

Organometallics

Volumn 18, Issue 25, 1999, Pages 5381-5394

  Wicht, Denyce K ^a   Kourkine, Igor V ^a   Kovacik, Ivan ^a   Glueck, David S ^a   Concolino, Thomas E ^b   Yap, Glenn P A ^b   Incarvito, Christopher D ^b   Rheingold, Arnold L ^b  

^a Dartmouth College   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000587455     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990745h     Document Type: Article

References (98)

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5. For some recent examples and leading references, see the following, (a) X = N: Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738-6744. (b) X = O: Bennett, M. A.; Jin, H.; Li, S.; Rendina, L. M.; Willis, A. C. J. Am. Chem. Soc. 1995, 117, 8335-8340. (c) X = B: Baker, R. T.; Calabrese, J. C.; Westcott, S. A.; Nguyen, P.; Marder, T. B. J. Am. Chem. Soc. 1993, 115, 4367-4368. (d) X = Si: Brookhart, M.; Grant, B. E. J. Am. Chem. Soc. 1993, 115, 2151-2156. (e) For analogous X-H additions with lanthanide catalysts, see: Arredondo, V. M.; Tian, S.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1999, 121, 3633-3639 and references therein.
6. For some recent examples and leading references, see the following, (a) X = N: Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738-6744. (b) X = O: Bennett, M. A.; Jin, H.; Li, S.; Rendina, L. M.; Willis, A. C. J. Am. Chem. Soc. 1995, 117, 8335-8340. (c) X = B: Baker, R. T.; Calabrese, J. C.; Westcott, S. A.; Nguyen, P.; Marder, T. B. J. Am. Chem. Soc. 1993, 115, 4367-4368. (d) X = Si: Brookhart, M.; Grant, B. E. J. Am. Chem. Soc. 1993, 115, 2151-2156. (e) For analogous X-H additions with lanthanide catalysts, see: Arredondo, V. M.; Tian, S.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1999, 121, 3633-3639 and references therein.
7. For some recent examples and leading references, see the following, (a) X = N: Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738-6744. (b) X = O: Bennett, M. A.; Jin, H.; Li, S.; Rendina, L. M.; Willis, A. C. J. Am. Chem. Soc. 1995, 117, 8335-8340. (c) X = B: Baker, R. T.; Calabrese, J. C.; Westcott, S. A.; Nguyen, P.; Marder, T. B. J. Am. Chem. Soc. 1993, 115, 4367-4368. (d) X = Si: Brookhart, M.; Grant, B. E. J. Am. Chem. Soc. 1993, 115, 2151-2156. (e) For analogous X-H additions with lanthanide catalysts, see: Arredondo, V. M.; Tian, S.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1999, 121, 3633-3639 and references therein.
8. For some recent examples and leading references, see the following, (a) X = N: Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. J. Am. Chem. Soc. 1988, 110, 6738-6744. (b) X = O: Bennett, M. A.; Jin, H.; Li, S.; Rendina, L. M.; Willis, A. C. J. Am. Chem. Soc. 1995, 117, 8335-8340. (c) X = B: Baker, R. T.; Calabrese, J. C.; Westcott, S. A.; Nguyen, P.; Marder, T. B. J. Am. Chem. Soc. 1993, 115, 4367-4368. (d) X = Si: Brookhart, M.; Grant, B. E. J. Am. Chem. Soc. 1993, 115, 2151-2156. (e) For analogous X-H additions with lanthanide catalysts, see: Arredondo, V. M.; Tian, S.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1999, 121, 3633-3639 and references therein.
9. Some of these results have been communicated previously: Wicht, D. K.; Kourkine, I. V.; Lew, B. M.; Nthenge, J. M.; Glueck, D. S. J. Am. Chem. Soc. 1997, 119, 5039-5040.
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17. For related chemistry, see: (g) Han, L.-B.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259-3261. (h) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571-1572. (i) Nagel, U.; Rieger, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223-239. (j) Han, L.-B.; Choi, N.; Tanaka, M. J. Am. Chem. Soc. 1998, 118, 7000-7001. (k) Han, L.-B.; Hua, R.; Tanaka, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 94-96.
18. For related chemistry, see: (g) Han, L.-B.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259-3261. (h) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571-1572. (i) Nagel, U.; Rieger, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223-239. (j) Han, L.-B.; Choi, N.; Tanaka, M. J. Am. Chem. Soc. 1998, 118, 7000-7001. (k) Han, L.-B.; Hua, R.; Tanaka, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 94-96.
19. For related chemistry, see: (g) Han, L.-B.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259-3261. (h) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571-1572. (i) Nagel, U.; Rieger, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223-239. (j) Han, L.-B.; Choi, N.; Tanaka, M. J. Am. Chem. Soc. 1998, 118, 7000-7001. (k) Han, L.-B.; Hua, R.; Tanaka, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 94-96.
20. For related chemistry, see: (g) Han, L.-B.; Choi, N.; Tanaka, M. Organometallics 1996, 15, 3259-3261. (h) Han, L.-B.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 1571-1572. (i) Nagel, U.; Rieger, B.; Bublewitz, A. J. Organomet. Chem. 1989, 370, 223-239. (j) Han, L.-B.; Choi, N.; Tanaka, M. J. Am. Chem. Soc. 1998, 118, 7000-7001. (k) Han, L.-B.; Hua, R.; Tanaka, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 94-96.
21. For lanthanide-catalyzed reactions, see: (l) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, The Netherlands, 1992; pp 35-51. (m) Groger, H.; Saida, Y.; Arai, S.; Martens, J.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 9291-9292. (n) Groger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089-3103.
22. For lanthanide-catalyzed reactions, see: (l) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, The Netherlands, 1992; pp 35-51. (m) Groger, H.; Saida, Y.; Arai, S.; Martens, J.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 9291-9292. (n) Groger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089-3103.
23. For lanthanide-catalyzed reactions, see: (l) Giardello, M. A.; King, W. A.; Nolan, S. P.; Porchia, M.; Sishta, C.; Marks, T. J. In Energetics of Organometallic Species; Martinho Simoes, J. A., Ed.; Kluwer: Dordrecht, The Netherlands, 1992; pp 35-51. (m) Groger, H.; Saida, Y.; Arai, S.; Martens, J.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 9291-9292. (n) Groger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089-3103.
24. Wicht, D. K.; Zhuravel, M. A.; Gregush, R. V.; Glueck, D. S.; Guzei, I. A.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 1998, 17, 1412-1419.
25. Vinokurova, G. M.; Nagaeva, K. K. Izv. Akad. Nauk SSSR, Ser. Khim. 1976, 414.
26. 2CN) (Organometallics) are commercially available.
27. 2CN) (Organometallics) are commercially available.
28. 2CN) (Organometallics) are commercially available.
29. 2CN) (Organometallics) are commercially available.
30. 2CN) (Organometallics) are commercially available.
31. 2CN) (Organometallics) are commercially available.
32. 31P NMR and by comparison to an authentic sample: Clark, H. C.; Kapoor, P. N.; McMahon, I. J. J. Organomet. Chem. 1984, 265, 107-115.
33. 2 also generates a small amount of 4
34. For examples of related disproportionations, see: (a) Bennett, M. A.; Chiraratvatana, C. J. Organomet. Chem. 1985, 296, 255-267. (b) Davies, J. A.; Eagle, C. T.; Otis, D. E.; Venkataraman, U. Organometallics 1989, 8, 1080-1088. (c) Reference 9.
35. For examples of related disproportionations, see: (a) Bennett, M. A.; Chiraratvatana, C. J. Organomet. Chem. 1985, 296, 255-267. (b) Davies, J. A.; Eagle, C. T.; Otis, D. E.; Venkataraman, U. Organometallics 1989, 8, 1080-1088. (c) Reference 9.
36. For examples of related disproportionations, see: (a) Bennett, M. A.; Chiraratvatana, C. J. Organomet. Chem. 1985, 296, 255-267. (b) Davies, J. A.; Eagle, C. T.; Otis, D. E.; Venkataraman, U. Organometallics 1989, 8, 1080-1088. (c) Reference 9.
37. 2py = 2-pyridyldiphenylphosphine) gives a cyanoethyl group: Xie, Y.; James, B. R. J. Organomet. Chem. 1991, 417, 277-288.
38. 4)(H) does not react with acrylonitrile in boiling n-hexane: Arnold, D. P.; Bennett, M. A. Inorg. Chem. 1984, 23, 2110-2116.
39. For examples of P-C reductive elimination, see: (a) Falvello, L. R.; Fornies, J.; Fortuno, C.; Martin, A.; Martinez-Sarinena, A. P. Organometallics 1997, 16, 5849-5856. (b) Archambault, C.; Bender, R.; Braunstein, P.; De Cian, A.; Fischer, J. Chem. Commun. 1996, 2729-2730. (c) Shulman, P. M.; Burkhardt, E. D.; Lundquist, E. G.; Pilato, R. S.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1987, 6, 101-109. (d) Geoffroy, G. L.; Rosenberg, S.; Shulman, P. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 1519-1521. (e) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724-8736. (f) Gaumont, A.-C.; Hursthouse, M. B.; Coles, S. J.; Brown, J. M. Chem. Commun. 1999, 63-64.
40. For examples of P-C reductive elimination, see: (a) Falvello, L. R.; Fornies, J.; Fortuno, C.; Martin, A.; Martinez-Sarinena, A. P. Organometallics 1997, 16, 5849-5856. (b) Archambault, C.; Bender, R.; Braunstein, P.; De Cian, A.; Fischer, J. Chem. Commun. 1996, 2729-2730. (c) Shulman, P. M.; Burkhardt, E. D.; Lundquist, E. G.; Pilato, R. S.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1987, 6, 101-109. (d) Geoffroy, G. L.; Rosenberg, S.; Shulman, P. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 1519-1521. (e) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724-8736. (f) Gaumont, A.-C.; Hursthouse, M. B.; Coles, S. J.; Brown, J. M. Chem. Commun. 1999, 63-64.
41. For examples of P-C reductive elimination, see: (a) Falvello, L. R.; Fornies, J.; Fortuno, C.; Martin, A.; Martinez-Sarinena, A. P. Organometallics 1997, 16, 5849-5856. (b) Archambault, C.; Bender, R.; Braunstein, P.; De Cian, A.; Fischer, J. Chem. Commun. 1996, 2729-2730. (c) Shulman, P. M.; Burkhardt, E. D.; Lundquist, E. G.; Pilato, R. S.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1987, 6, 101-109. (d) Geoffroy, G. L.; Rosenberg, S.; Shulman, P. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 1519-1521. (e) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724-8736. (f) Gaumont, A.-C.; Hursthouse, M. B.; Coles, S. J.; Brown, J. M. Chem. Commun. 1999, 63-64.
42. For examples of P-C reductive elimination, see: (a) Falvello, L. R.; Fornies, J.; Fortuno, C.; Martin, A.; Martinez-Sarinena, A. P. Organometallics 1997, 16, 5849-5856. (b) Archambault, C.; Bender, R.; Braunstein, P.; De Cian, A.; Fischer, J. Chem. Commun. 1996, 2729-2730. (c) Shulman, P. M.; Burkhardt, E. D.; Lundquist, E. G.; Pilato, R. S.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1987, 6, 101-109. (d) Geoffroy, G. L.; Rosenberg, S.; Shulman, P. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 1519-1521. (e) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724-8736. (f) Gaumont, A.-C.; Hursthouse, M. B.; Coles, S. J.; Brown, J. M. Chem. Commun. 1999, 63-64.
43. For examples of P-C reductive elimination, see: (a) Falvello, L. R.; Fornies, J.; Fortuno, C.; Martin, A.; Martinez-Sarinena, A. P. Organometallics 1997, 16, 5849-5856. (b) Archambault, C.; Bender, R.; Braunstein, P.; De Cian, A.; Fischer, J. Chem. Commun. 1996, 2729-2730. (c) Shulman, P. M.; Burkhardt, E. D.; Lundquist, E. G.; Pilato, R. S.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1987, 6, 101-109. (d) Geoffroy, G. L.; Rosenberg, S.; Shulman, P. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 1519-1521. (e) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724-8736. (f) Gaumont, A.-C.; Hursthouse, M. B.; Coles, S. J.; Brown, J. M. Chem. Commun. 1999, 63-64.
44. For examples of P-C reductive elimination, see: (a) Falvello, L. R.; Fornies, J.; Fortuno, C.; Martin, A.; Martinez-Sarinena, A. P. Organometallics 1997, 16, 5849-5856. (b) Archambault, C.; Bender, R.; Braunstein, P.; De Cian, A.; Fischer, J. Chem. Commun. 1996, 2729-2730. (c) Shulman, P. M.; Burkhardt, E. D.; Lundquist, E. G.; Pilato, R. S.; Geoffroy, G. L.; Rheingold, A. L. Organometallics 1987, 6, 101-109. (d) Geoffroy, G. L.; Rosenberg, S.; Shulman, P. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 1519-1521. (e) Fryzuk, M. D.; Joshi, K.; Chadha, R. K.; Rettig, S. J. J. Am. Chem. Soc. 1991, 113, 8724-8736. (f) Gaumont, A.-C.; Hursthouse, M. B.; Coles, S. J.; Brown, J. M. Chem. Commun. 1999, 63-64.
45. 2Mes*, and because this reaction in the absence of catalyst is slow. Dimesitylphosphido complex 10 was prepared for comparison.
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49. 16 See the Supporting Information for details of the thermolyses of 9-13.
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51. (b) Reger, D. L.; Garza, D. G.; Lebioda, L. Organometallics 1992, 11, 4285-4292.
52. (c) Reger, D. L.; McElligott, P. J. J. Organomet. Chem. 1981, 216, C12-C14.
53. (d) Reger, D. L. Inorg. Chem. 1975, 14, 660-664.
54. (e) See also ref 15.
55. For related examples in which the lone pair of a pendant amino or phosphido ligand coordinates to the metal center, see: (a) Reference 3a. (b) Hegedus, L. S.; Akermark, B.; Zetterberg, K.; Olsson, L. F. J. Am. Chem. Soc. 1984, 206, 7122-7126. (c) Hey-Hawkins, E.; Kurz, S.; Sieler, J.; Baum, G. J. Organomet. Chem. 1995, 486, 229-235.
56. For related examples in which the lone pair of a pendant amino or phosphido ligand coordinates to the metal center, see: (a) Reference 3a. (b) Hegedus, L. S.; Akermark, B.; Zetterberg, K.; Olsson, L. F. J. Am. Chem. Soc. 1984, 206, 7122-7126. (c) Hey-Hawkins, E.; Kurz, S.; Sieler, J.; Baum, G. J. Organomet. Chem. 1995, 486, 229-235.
57. For related examples in which the lone pair of a pendant amino or phosphido ligand coordinates to the metal center, see: (a) Reference 3a. (b) Hegedus, L. S.; Akermark, B.; Zetterberg, K.; Olsson, L. F. J. Am. Chem. Soc. 1984, 206, 7122-7126. (c) Hey-Hawkins, E.; Kurz, S.; Sieler, J.; Baum, G. J. Organomet. Chem. 1995, 486, 229-235.
58. 31P NMR spectrum of 15 was unchanged at -75 °C.
59. 31P NMR: (a) Yoshifuji, M.; Shibayama, K.; Inamoto, N. Chem. Lett. 1984, 115-118. (b) Brauer, D. J.; Bitterer, F.; Dorrenbach, F.; Hessler, G.; Stelzer, O.; Kruger, C.; Lutz, F. Z. Naturforsch., B 1996, 51, 1183-1196.
60. 31P NMR: (a) Yoshifuji, M.; Shibayama, K.; Inamoto, N. Chem. Lett. 1984, 115-118. (b) Brauer, D. J.; Bitterer, F.; Dorrenbach, F.; Hessler, G.; Stelzer, O.; Kruger, C.; Lutz, F. Z. Naturforsch., B 1996, 51, 1183-1196.
61. 31P NMR and comparison to an authentic sample. Further results on this and related reductive eliminations in palladium phosphido complexes will be reported separately: Zhuravel, M. A.; Wicht, D. K.; Nthenge, J. M.; Sweeder, R. D.; Glueck, D. S. Manuscript in preparation.
62. For a review, see: Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163-1188.
63. (a) Bryndza, H. E. Organometallics 1985, 4, 406-408.
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65. +, see: Dockter, D. W.; Fanwick, P. E.; Kubiak, C. P. J. Am. Chem. Soc. 1996, 118, 4846-4852.
66. (d) See also ref 3b.
67. Rees, W. M.; Churchill, M. R.; Fettinger, J. C.; Atwood, J. D. Organometallics 1985, 4, 2179-2185.
68. 31P NMR spectrum and by irreproducible results of IR spectra, which showed a variety of CN stretches depending on sample history and anion. Complex 19 decomposed over a period of days in methylene chloride solution under nitrogen.
69. Pt-P = 4370 Hz): Appleton, T. G.; Bennett, M. A. Inorg. Chem. 1978, 17, 738-747.
70. 4] (R = Me, H), see: Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 202, 107-114.
71. 4] (R = Me, H), see: Arnold, D. P.; Bennett, M. A. J. Organomet. Chem. 1980, 202, 107-114.
72. (b) For a review of acrylonitrile coordination chemistry, see: Bryan, S. J.; Huggett, P. G.; Wade, K.; Daniels, J. A.; Jennings, J. R. Coord. Chem. Rev. 1982, 44, 149-189.
73. (c) For a recent report of an analogous cationic Pt diazabutadiene complex with π-bound acrylonitrile, see: Yang, K.; Lachicotte, R. J.; Eisenberg, R. Organometallics 1998, 17, 5102-5113. However, this complex has recently been reformulated as N-bound. See: Albietz, P. J., Jr.; Yang, K.; Eisenberg, R. Organometallics 1999, 18, 2747-2749.
74. (c) For a recent report of an analogous cationic Pt diazabutadiene complex with π-bound acrylonitrile, see: Yang, K.; Lachicotte, R. J.; Eisenberg, R. Organometallics 1998, 17, 5102-5113. However, this complex has recently been reformulated as N-bound. See: Albietz, P. J., Jr.; Yang, K.; Eisenberg, R. Organometallics 1999, 18, 2747-2749.
75. Bartlett, R. A.; Olmstead, M. M.; Power, P. P.; Sigel, G. A. Inorg. Chem. 1987, 26, 1941-1946.
76. 2CN without isolation of an intermediate. See: Cowan, R. L.; Trogler, W. C. J. Am. Chem. Soc. 1989, 111, 4750-4761.
77. 2), see: Edelbach, B. L.; Vicic, D. A.; Lachicotte, R. J.; Jones, W. D. Organometallics 1998, 17, 4784-4794.
78. 2), see: Edelbach, B. L.; Vicic, D. A.; Lachicotte, R. J.; Jones, W. D. Organometallics 1998, 17, 4784-4794.
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83. (a) Ros, R.; Michelin, R. A.; Bataillard, R.; Roulet, R. J. Organomet. Chem. 1977, 139, 355-359.
84. (b) Reference 11b.
85. For examples, see: (a) Komiya, S.; Abe, Y.; Yamamoto, A.; Yamamoto, T. Organometallics 1983, 2, 1466-1468. (b) McKinney, R. J.; Roe, C. D. J. Am. Chem. Soc. 1985, 107, 262-264 and references therein. (c) Kohara, T.; Yamamoto, T.; Yamamoto, A. J. Organomet. Chem. 1980, 192, 265-274. For theoretical discussion, see: (d) Tatsumi, K.; Nakamura, A.; Komiya, S.; Yamamoto, A.; Yamamoto, T. J. Am. Chem. Soc. 1984, 106, 8181-8188. (e) See also ref 31 and: Seligson, A. L.; Cowan, R. L.; Trogler, W. C. Inorg. Chem. 1991, 30, 3371-3381.
86. For examples, see: (a) Komiya, S.; Abe, Y.; Yamamoto, A.; Yamamoto, T. Organometallics 1983, 2, 1466-1468. (b) McKinney, R. J.; Roe, C. D. J. Am. Chem. Soc. 1985, 107, 262-264 and references therein. (c) Kohara, T.; Yamamoto, T.; Yamamoto, A. J. Organomet. Chem. 1980, 192, 265-274. For theoretical discussion, see: (d) Tatsumi, K.; Nakamura, A.; Komiya, S.; Yamamoto, A.; Yamamoto, T. J. Am. Chem. Soc. 1984, 106, 8181-8188. (e) See also ref 31 and: Seligson, A. L.; Cowan, R. L.; Trogler, W. C. Inorg. Chem. 1991, 30, 3371-3381.
87. For examples, see: (a) Komiya, S.; Abe, Y.; Yamamoto, A.; Yamamoto, T. Organometallics 1983, 2, 1466-1468. (b) McKinney, R. J.; Roe, C. D. J. Am. Chem. Soc. 1985, 107, 262-264 and references therein. (c) Kohara, T.; Yamamoto, T.; Yamamoto, A. J. Organomet. Chem. 1980, 192, 265-274. For theoretical discussion, see: (d) Tatsumi, K.; Nakamura, A.; Komiya, S.; Yamamoto, A.; Yamamoto, T. J. Am. Chem. Soc. 1984, 106, 8181-8188. (e) See also ref 31 and: Seligson, A. L.; Cowan, R. L.; Trogler, W. C. Inorg. Chem. 1991, 30, 3371-3381.
88. For examples, see: (a) Komiya, S.; Abe, Y.; Yamamoto, A.; Yamamoto, T. Organometallics 1983, 2, 1466-1468. (b) McKinney, R. J.; Roe, C. D. J. Am. Chem. Soc. 1985, 107, 262-264 and references therein. (c) Kohara, T.; Yamamoto, T.; Yamamoto, A. J. Organomet. Chem. 1980, 192, 265-274. For theoretical discussion, see: (d) Tatsumi, K.; Nakamura, A.; Komiya, S.; Yamamoto, A.; Yamamoto, T. J. Am. Chem. Soc. 1984, 106, 8181-8188. (e) See also ref 31 and: Seligson, A. L.; Cowan, R. L.; Trogler, W. C. Inorg. Chem. 1991, 30, 3371-3381.
89. For examples, see: (a) Komiya, S.; Abe, Y.; Yamamoto, A.; Yamamoto, T. Organometallics 1983, 2, 1466-1468. (b) McKinney, R. J.; Roe, C. D. J. Am. Chem. Soc. 1985, 107, 262-264 and references therein. (c) Kohara, T.; Yamamoto, T.; Yamamoto, A. J. Organomet. Chem. 1980, 192, 265-274. For theoretical discussion, see: (d) Tatsumi, K.; Nakamura, A.; Komiya, S.; Yamamoto, A.; Yamamoto, T. J. Am. Chem. Soc. 1984, 106, 8181-8188. (e) See also ref 31 and: Seligson, A. L.; Cowan, R. L.; Trogler, W. C. Inorg. Chem. 1991, 30, 3371-3381.
90. Four-membered metallacycles have been observed in olefin hydroamination. For examples, see ref 20a,b.
91. 1H NMR. Full details will be reported separately.
92. For other examples of olefin-induced X-H reductive elimination, see: (a) Glueck, D. S.; Newman Winslow, L. J.; Bergman, R. G. Organometallics 1991, 10, 1462-1479. (b) Hauger, B.; Caulton, K. G. J. Organomet. Chem. 1983, 450, 253-261. (c) Reference 36e.
93. For other examples of olefin-induced X-H reductive elimination, see: (a) Glueck, D. S.; Newman Winslow, L. J.; Bergman, R. G. Organometallics 1991, 10, 1462-1479. (b) Hauger, B.; Caulton, K. G. J. Organomet. Chem. 1983, 450, 253-261. (c) Reference 36e.
94. For other examples of olefin-induced X-H reductive elimination, see: (a) Glueck, D. S.; Newman Winslow, L. J.; Bergman, R. G. Organometallics 1991, 10, 1462-1479. (b) Hauger, B.; Caulton, K. G. J. Organomet. Chem. 1983, 450, 253-261. (c) Reference 36e.
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