Ligand metalation in triisopropylphosphine-platinum(II) compounds

Organometallics

Volumn 17, Issue 3, 1998, Pages 348-352

  Thorn, David L ^a  

^a DUPONT COMPANY   (United States)

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EID: 0003375993     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970759s     Document Type: Article

References (31)

1. See, for example: Cheney, A. J.; Mann, B. E.; Shaw, B. L.; Slade, R. M. J. Chem. Soc. Chem. Commun. 1970, 1176-1177. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972-1982. Al-Salem, N. A.; McDonald, W. S.; Markham, R.; Norton, M. C.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 59-63. Clark, H. C.; Goel, A. B.; Goel, R. G.; Goel, S. Inorg. Chem. 1980, 19, 3220-3225. Goel, A. B.; Goel, S.; Vanderveer, D. Inorg. Chim. Acta 1981, 54, L267-L269. Goel, R. G.; Ogini, W. O.; Srivastava, R. C. Organometallics 1982, 1, 819-824. Simms, B. L.; Shang, M.; Lu, J.; Youngs. W. J.; Ibers, J. A. Organometallics 1987, 6, 1118-1126. Alyea, E. C.; Malito, J. J. Organometal. Chem. 1988, 340, 119-126. Alyea, E. C.; Ferguson, G.; Malito, J.; Ruhl, B. L. Organometallics 1989, 8, 1188-1191. Minghetti, G.; Cinellu, M. A.; Stoccoro, S.; Zucca, A.; Manassero, M. J. Chem. Soc., Dalton Trans. 1995, 777-781.
2. See, for example: Cheney, A. J.; Mann, B. E.; Shaw, B. L.; Slade, R. M. J. Chem. Soc. Chem. Commun. 1970, 1176-1177. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972-1982. Al-Salem, N. A.; McDonald, W. S.; Markham, R.; Norton, M. C.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 59-63. Clark, H. C.; Goel, A. B.; Goel, R. G.; Goel, S. Inorg. Chem. 1980, 19, 3220-3225. Goel, A. B.; Goel, S.; Vanderveer, D. Inorg. Chim. Acta 1981, 54, L267-L269. Goel, R. G.; Ogini, W. O.; Srivastava, R. C. Organometallics 1982, 1, 819-824. Simms, B. L.; Shang, M.; Lu, J.; Youngs. W. J.; Ibers, J. A. Organometallics 1987, 6, 1118-1126. Alyea, E. C.; Malito, J. J. Organometal. Chem. 1988, 340, 119-126. Alyea, E. C.; Ferguson, G.; Malito, J.; Ruhl, B. L. Organometallics 1989, 8, 1188-1191. Minghetti, G.; Cinellu, M. A.; Stoccoro, S.; Zucca, A.; Manassero, M. J. Chem. Soc., Dalton Trans. 1995, 777-781.
3. See, for example: Cheney, A. J.; Mann, B. E.; Shaw, B. L.; Slade, R. M. J. Chem. Soc. Chem. Commun. 1970, 1176-1177. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972-1982. Al-Salem, N. A.; McDonald, W. S.; Markham, R.; Norton, M. C.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 59-63. Clark, H. C.; Goel, A. B.; Goel, R. G.; Goel, S. Inorg. Chem. 1980, 19, 3220-3225. Goel, A. B.; Goel, S.; Vanderveer, D. Inorg. Chim. Acta 1981, 54, L267-L269. Goel, R. G.; Ogini, W. O.; Srivastava, R. C. Organometallics 1982, 1, 819-824. Simms, B. L.; Shang, M.; Lu, J.; Youngs. W. J.; Ibers, J. A. Organometallics 1987, 6, 1118-1126. Alyea, E. C.; Malito, J. J. Organometal. Chem. 1988, 340, 119-126. Alyea, E. C.; Ferguson, G.; Malito, J.; Ruhl, B. L. Organometallics 1989, 8, 1188-1191. Minghetti, G.; Cinellu, M. A.; Stoccoro, S.; Zucca, A.; Manassero, M. J. Chem. Soc., Dalton Trans. 1995, 777-781.
4. See, for example: Cheney, A. J.; Mann, B. E.; Shaw, B. L.; Slade, R. M. J. Chem. Soc. Chem. Commun. 1970, 1176-1177. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972-1982. Al-Salem, N. A.; McDonald, W. S.; Markham, R.; Norton, M. C.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 59-63. Clark, H. C.; Goel, A. B.; Goel, R. G.; Goel, S. Inorg. Chem. 1980, 19, 3220-3225. Goel, A. B.; Goel, S.; Vanderveer, D. Inorg. Chim. Acta 1981, 54, L267-L269. Goel, R. G.; Ogini, W. O.; Srivastava, R. C. Organometallics 1982, 1, 819-824. Simms, B. L.; Shang, M.; Lu, J.; Youngs. W. J.; Ibers, J. A. Organometallics 1987, 6, 1118-1126. Alyea, E. C.; Malito, J. J. Organometal. Chem. 1988, 340, 119-126. Alyea, E. C.; Ferguson, G.; Malito, J.; Ruhl, B. L. Organometallics 1989, 8, 1188-1191. Minghetti, G.; Cinellu, M. A.; Stoccoro, S.; Zucca, A.; Manassero, M. J. Chem. Soc., Dalton Trans. 1995, 777-781.
5. See, for example: Cheney, A. J.; Mann, B. E.; Shaw, B. L.; Slade, R. M. J. Chem. Soc. Chem. Commun. 1970, 1176-1177. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972-1982. Al-Salem, N. A.; McDonald, W. S.; Markham, R.; Norton, M. C.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 59-63. Clark, H. C.; Goel, A. B.; Goel, R. G.; Goel, S. Inorg. Chem. 1980, 19, 3220-3225. Goel, A. B.; Goel, S.; Vanderveer, D. Inorg. Chim. Acta 1981, 54, L267-L269. Goel, R. G.; Ogini, W. O.; Srivastava, R. C. Organometallics 1982, 1, 819-824. Simms, B. L.; Shang, M.; Lu, J.; Youngs. W. J.; Ibers, J. A. Organometallics 1987, 6, 1118-1126. Alyea, E. C.; Malito, J. J. Organometal. Chem. 1988, 340, 119-126. Alyea, E. C.; Ferguson, G.; Malito, J.; Ruhl, B. L. Organometallics 1989, 8, 1188-1191. Minghetti, G.; Cinellu, M. A.; Stoccoro, S.; Zucca, A.; Manassero, M. J. Chem. Soc., Dalton Trans. 1995, 777-781.
6. See, for example: Cheney, A. J.; Mann, B. E.; Shaw, B. L.; Slade, R. M. J. Chem. Soc. Chem. Commun. 1970, 1176-1177. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972-1982. Al-Salem, N. A.; McDonald, W. S.; Markham, R.; Norton, M. C.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 59-63. Clark, H. C.; Goel, A. B.; Goel, R. G.; Goel, S. Inorg. Chem. 1980, 19, 3220-3225. Goel, A. B.; Goel, S.; Vanderveer, D. Inorg. Chim. Acta 1981, 54, L267-L269. Goel, R. G.; Ogini, W. O.; Srivastava, R. C. Organometallics 1982, 1, 819-824. Simms, B. L.; Shang, M.; Lu, J.; Youngs. W. J.; Ibers, J. A. Organometallics 1987, 6, 1118-1126. Alyea, E. C.; Malito, J. J. Organometal. Chem. 1988, 340, 119-126. Alyea, E. C.; Ferguson, G.; Malito, J.; Ruhl, B. L. Organometallics 1989, 8, 1188-1191. Minghetti, G.; Cinellu, M. A.; Stoccoro, S.; Zucca, A.; Manassero, M. J. Chem. Soc., Dalton Trans. 1995, 777-781.
7. See, for example: Cheney, A. J.; Mann, B. E.; Shaw, B. L.; Slade, R. M. J. Chem. Soc. Chem. Commun. 1970, 1176-1177. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972-1982. Al-Salem, N. A.; McDonald, W. S.; Markham, R.; Norton, M. C.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 59-63. Clark, H. C.; Goel, A. B.; Goel, R. G.; Goel, S. Inorg. Chem. 1980, 19, 3220-3225. Goel, A. B.; Goel, S.; Vanderveer, D. Inorg. Chim. Acta 1981, 54, L267-L269. Goel, R. G.; Ogini, W. O.; Srivastava, R. C. Organometallics 1982, 1, 819-824. Simms, B. L.; Shang, M.; Lu, J.; Youngs. W. J.; Ibers, J. A. Organometallics 1987, 6, 1118-1126. Alyea, E. C.; Malito, J. J. Organometal. Chem. 1988, 340, 119-126. Alyea, E. C.; Ferguson, G.; Malito, J.; Ruhl, B. L. Organometallics 1989, 8, 1188-1191. Minghetti, G.; Cinellu, M. A.; Stoccoro, S.; Zucca, A.; Manassero, M. J. Chem. Soc., Dalton Trans. 1995, 777-781.
8. See, for example: Cheney, A. J.; Mann, B. E.; Shaw, B. L.; Slade, R. M. J. Chem. Soc. Chem. Commun. 1970, 1176-1177. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972-1982. Al-Salem, N. A.; McDonald, W. S.; Markham, R.; Norton, M. C.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 59-63. Clark, H. C.; Goel, A. B.; Goel, R. G.; Goel, S. Inorg. Chem. 1980, 19, 3220-3225. Goel, A. B.; Goel, S.; Vanderveer, D. Inorg. Chim. Acta 1981, 54, L267-L269. Goel, R. G.; Ogini, W. O.; Srivastava, R. C. Organometallics 1982, 1, 819-824. Simms, B. L.; Shang, M.; Lu, J.; Youngs. W. J.; Ibers, J. A. Organometallics 1987, 6, 1118-1126. Alyea, E. C.; Malito, J. J. Organometal. Chem. 1988, 340, 119-126. Alyea, E. C.; Ferguson, G.; Malito, J.; Ruhl, B. L. Organometallics 1989, 8, 1188-1191. Minghetti, G.; Cinellu, M. A.; Stoccoro, S.; Zucca, A.; Manassero, M. J. Chem. Soc., Dalton Trans. 1995, 777-781.
9. See, for example: Cheney, A. J.; Mann, B. E.; Shaw, B. L.; Slade, R. M. J. Chem. Soc. Chem. Commun. 1970, 1176-1177. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972-1982. Al-Salem, N. A.; McDonald, W. S.; Markham, R.; Norton, M. C.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 59-63. Clark, H. C.; Goel, A. B.; Goel, R. G.; Goel, S. Inorg. Chem. 1980, 19, 3220-3225. Goel, A. B.; Goel, S.; Vanderveer, D. Inorg. Chim. Acta 1981, 54, L267-L269. Goel, R. G.; Ogini, W. O.; Srivastava, R. C. Organometallics 1982, 1, 819-824. Simms, B. L.; Shang, M.; Lu, J.; Youngs. W. J.; Ibers, J. A. Organometallics 1987, 6, 1118-1126. Alyea, E. C.; Malito, J. J. Organometal. Chem. 1988, 340, 119-126. Alyea, E. C.; Ferguson, G.; Malito, J.; Ruhl, B. L. Organometallics 1989, 8, 1188-1191. Minghetti, G.; Cinellu, M. A.; Stoccoro, S.; Zucca, A.; Manassero, M. J. Chem. Soc., Dalton Trans. 1995, 777-781.
10. See, for example: Cheney, A. J.; Mann, B. E.; Shaw, B. L.; Slade, R. M. J. Chem. Soc. Chem. Commun. 1970, 1176-1177. Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Shaw, B. L.; Weeks, B. J. Chem. Soc., Dalton Trans. 1979, 1972-1982. Al-Salem, N. A.; McDonald, W. S.; Markham, R.; Norton, M. C.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 59-63. Clark, H. C.; Goel, A. B.; Goel, R. G.; Goel, S. Inorg. Chem. 1980, 19, 3220-3225. Goel, A. B.; Goel, S.; Vanderveer, D. Inorg. Chim. Acta 1981, 54, L267-L269. Goel, R. G.; Ogini, W. O.; Srivastava, R. C. Organometallics 1982, 1, 819-824. Simms, B. L.; Shang, M.; Lu, J.; Youngs. W. J.; Ibers, J. A. Organometallics 1987, 6, 1118-1126. Alyea, E. C.; Malito, J. J. Organometal. Chem. 1988, 340, 119-126. Alyea, E. C.; Ferguson, G.; Malito, J.; Ruhl, B. L. Organometallics 1989, 8, 1188-1191. Minghetti, G.; Cinellu, M. A.; Stoccoro, S.; Zucca, A.; Manassero, M. J. Chem. Soc., Dalton Trans. 1995, 777-781.
11. Van der Boom, M. E.; Liou, S.-Y.; Shimon, L. J. W.; Ben-David, Y.; Milstein, D. Organometallics 1996, 15, 2562-2568.
12. Probably, when HCl (or HOTf and a chloride source) is added to alkyltriflatoPt 1 or 2, the reaction actually proceeds by Cl/triflate exchange to first make the corresponding chloro(alkyl)platinum compound and HOTf, which then react.
13. x similar to the (monophosphine)(methyl)palladium compounds described by Kayaki, Y.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1997, 70, 1141-1147.
14. 3 bonds has been discussed recently by: Hill, G. S.; Rendina, L. M.; Puddephatt, R. J. Organometallics 1995, 14, 4966-4968. Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1995, 117, 9371-9372. Stahl, S. S.; Labinger, J. A.; Bercaw, J. Am. Chem. Soc. 1996, 118, 5961-5976. There has been some controversy over the precise mechanism and earlier articles are referenced therein.
15. 3 bonds has been discussed recently by: Hill, G. S.; Rendina, L. M.; Puddephatt, R. J. Organometallics 1995, 14, 4966-4968. Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1995, 117, 9371-9372. Stahl, S. S.; Labinger, J. A.; Bercaw, J. Am. Chem. Soc. 1996, 118, 5961-5976. There has been some controversy over the precise mechanism and earlier articles are referenced therein.
16. 3 bonds has been discussed recently by: Hill, G. S.; Rendina, L. M.; Puddephatt, R. J. Organometallics 1995, 14, 4966-4968. Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1995, 117, 9371-9372. Stahl, S. S.; Labinger, J. A.; Bercaw, J. Am. Chem. Soc. 1996, 118, 5961-5976. There has been some controversy over the precise mechanism and earlier articles are referenced therein.
17. The chloride redistribution reaction, eq 3b, is observed whenever significant concentrations of 3 and 5 are simultaneously present. The successful preparation of 3 from 5 (Scheme 1) requires the rapid addition of stoichiometric HOTf; if less than 1 equiv of HOTf is used, 1 and 6 become major products.
18. Zhang, L.; Zetterberg, K. Organometallics 1991, 10, 3806-3813.
19. Ryabov, A. D.; van Eldik, R. Angew. Chem. 1994, 106, 798; Angew. Chem., Int. Ed. Engl. 1994, 33, 783-784.
20. Ryabov, A. D.; van Eldik, R. Angew. Chem. 1994, 106, 798; Angew. Chem., Int. Ed. Engl. 1994, 33, 783-784.
21. Exchange with alkanes is exhibited by (solvento)(methyl)Ir (Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517-2518. Arndtsen, B. A.; Bergman, R. G. Science 1995, 270, 1970-1973. Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462-10463) and (solvente)(methyl)Pt (Holtcamp, M. W.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1997, 119, 848-849). In these compounds of the late transition metals, the actual mechanism of such alkyl group exchange is likely to be oxidative addition/reductive elimination of H-C bonds. Alkyl compounds of the early transition metals exchange with alkanes by mechanisms more closely approximating true σ-bond metathesis.
22. Exchange with alkanes is exhibited by (solvento)(methyl)Ir (Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517-2518. Arndtsen, B. A.; Bergman, R. G. Science 1995, 270, 1970-1973. Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462-10463) and (solvente)(methyl)Pt (Holtcamp, M. W.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1997, 119, 848-849). In these compounds of the late transition metals, the actual mechanism of such alkyl group exchange is likely to be oxidative addition/reductive elimination of H-C bonds. Alkyl compounds of the early transition metals exchange with alkanes by mechanisms more closely approximating true σ-bond metathesis.
23. Exchange with alkanes is exhibited by (solvento)(methyl)Ir (Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517-2518. Arndtsen, B. A.; Bergman, R. G. Science 1995, 270, 1970-1973. Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462-10463) and (solvente)(methyl)Pt (Holtcamp, M. W.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1997, 119, 848-849). In these compounds of the late transition metals, the actual mechanism of such alkyl group exchange is likely to be oxidative addition/reductive elimination of H-C bonds. Alkyl compounds of the early transition metals exchange with alkanes by mechanisms more closely approximating true σ-bond metathesis.
24. Exchange with alkanes is exhibited by (solvento)(methyl)Ir (Luecke, H. F.; Arndtsen, B. A.; Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 2517-2518. Arndtsen, B. A.; Bergman, R. G. Science 1995, 270, 1970-1973. Burger, P.; Bergman, R. G. J. Am. Chem. Soc. 1993, 115, 10462-10463) and (solvente)(methyl)Pt (Holtcamp, M. W.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1997, 119, 848-849). In these compounds of the late transition metals, the actual mechanism of such alkyl group exchange is likely to be oxidative addition/reductive elimination of H-C bonds. Alkyl compounds of the early transition metals exchange with alkanes by mechanisms more closely approximating true σ-bond metathesis.
25. 31P NMR signals consistent with the presence of metalated compounds.
26. Tricyclohexylphosphine-platinum and tricyclopentylphosphine-platinum compounds analogous to the triisopropylphosphine-platinum compounds described herein behave similarly, except the cyclohexyl group provides a more complex set of metalated products (not fully characterized), some of which eventually lead to hydridoplatinum compounds.
27. 9 In this reaction, loss of the triflato ligand is a critical component, as the reaction occurs much more rapidly when the triflato ligand is replaced by solvent.
28. Rapid ligand metalation by electrophilic Ir(III) compounds has been demonstrated; see: Simpson, R. D. Organometallics 1997, 16, 1797-1799. Cooper, A. C.; Huffman, J. C.; Caulton, K. G. Organometallics 1997, 16, 1974-1978.
29. Rapid ligand metalation by electrophilic Ir(III) compounds has been demonstrated; see: Simpson, R. D. Organometallics 1997, 16, 1797-1799. Cooper, A. C.; Huffman, J. C.; Caulton, K. G. Organometallics 1997, 16, 1974-1978.
30. Reamey, R. H.; Whitesides, G. M. J. Am. Chem. Soc. 1984, 106, 81-85.
31. Yoshida, T.; Matsuda, T.; Otsuka, S. Inorganic Syntheses; Wiley-Interscience: New York, 1979; Vol. 19, pp 107-110.