Dimethyl cuprate undergoes C-C bond coupling with methyliodide in the gas phase but dimethyl argenate does not

Organic Letters

Volumn 6, Issue 16, 2004, Pages 2761-2764

  James, Patrick F ^a   O'Hair, Richard A J ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; DIMETHYL ARGENATE; DIMETHYL CUPRATE; METHYL GROUP; METHYL IODIDE; SILVER; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CROSS COUPLING REACTION; GAS; PHASE TRANSITION; REACTION ANALYSIS; SYNTHESIS;

EID: 4344592906     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049003x     Document Type: Article

References (47)

1. For reviews and monographs on organocopper species, see: (a) Modern Organocopper Chemistry, Krause, N., Ed.; Wiley-VCH: Weinheim, 2002. (b) Lipshutz, B. H. Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, UK, 1994; pp 283-382. (c) Organocopper Reagents: A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, UK, 1994.
2. For reviews and monographs on organocopper species, see: (a) Modern Organocopper Chemistry, Krause, N., Ed.; Wiley-VCH: Weinheim, 2002. (b) Lipshutz, B. H. Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, UK, 1994; pp 283-382. (c) Organocopper Reagents: A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, UK, 1994.
3. For reviews and monographs on organocopper species, see: (a) Modern Organocopper Chemistry, Krause, N., Ed.; Wiley-VCH: Weinheim, 2002. (b) Lipshutz, B. H. Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, UK, 1994; pp 283-382. (c) Organocopper Reagents: A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, UK, 1994.
4. For an excellent account of Gilman's research, see: Eisch, J. J., Organometallics 2002, 21, 5439.
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10. For an excellent review focusing on mechanistic aspects, see: Nakamura, E.; Mori, S. Angew. Chem., Int. Ed. 2000, 39, 3751.
11. For theoretical studies relevant to C-C bond coupling with alkyl halides, see: (a) Mori, S.; Hirai, A.; Nakamura, M.; Nakamura, E. Tetrahedron 2000, 56, 2805. (b) Mori, S.; Nakamura, E. Tetrahedron Lett. 1999, 40, 5319. (c) Nakamura, E.; Yamanaka, M.; Yoshikai, N.; Mori, S. Angew. Chem., Int. Ed. 2001, 40, 1935. (d) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 8273.
12. For theoretical studies relevant to C-C bond coupling with alkyl halides, see: (a) Mori, S.; Hirai, A.; Nakamura, M.; Nakamura, E. Tetrahedron 2000, 56, 2805. (b) Mori, S.; Nakamura, E. Tetrahedron Lett. 1999, 40, 5319. (c) Nakamura, E.; Yamanaka, M.; Yoshikai, N.; Mori, S. Angew. Chem., Int. Ed. 2001, 40, 1935. (d) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 8273.
13. For theoretical studies relevant to C-C bond coupling with alkyl halides, see: (a) Mori, S.; Hirai, A.; Nakamura, M.; Nakamura, E. Tetrahedron 2000, 56, 2805. (b) Mori, S.; Nakamura, E. Tetrahedron Lett. 1999, 40, 5319. (c) Nakamura, E.; Yamanaka, M.; Yoshikai, N.; Mori, S. Angew. Chem., Int. Ed. 2001, 40, 1935. (d) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 8273.
14. For theoretical studies relevant to C-C bond coupling with alkyl halides, see: (a) Mori, S.; Hirai, A.; Nakamura, M.; Nakamura, E. Tetrahedron 2000, 56, 2805. (b) Mori, S.; Nakamura, E. Tetrahedron Lett. 1999, 40, 5319. (c) Nakamura, E.; Yamanaka, M.; Yoshikai, N.; Mori, S. Angew. Chem., Int. Ed. 2001, 40, 1935. (d) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 8273.
15. Cu(III) have been implicated in the cross-coupling reactions of allylic esters with diallylcuprate species: Karlstrom, A. S. E.; Backvall, J. E. Chem. Eur. J. 2001, 7, 1981.
16. For theoretical studies on relevant Cu(III) species, see: (a) Nakamura, E.; Yamanaka, M.; Mori, S. J. Am. Chem. Soc. 2000, 122, 1826. (b) Nakamura, E.; Yamanaka, M. J. Am. Chem. Soc. 1999, 121, 8941. (c) Dorigo A. E.; Wanner J.; Schleyer, P. V. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 476. (d) Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11025.
17. For theoretical studies on relevant Cu(III) species, see: (a) Nakamura, E.; Yamanaka, M.; Mori, S. J. Am. Chem. Soc. 2000, 122, 1826. (b) Nakamura, E.; Yamanaka, M. J. Am. Chem. Soc. 1999, 121, 8941. (c) Dorigo A. E.; Wanner J.; Schleyer, P. V. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 476. (d) Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11025.
18. For theoretical studies on relevant Cu(III) species, see: (a) Nakamura, E.; Yamanaka, M.; Mori, S. J. Am. Chem. Soc. 2000, 122, 1826. (b) Nakamura, E.; Yamanaka, M. J. Am. Chem. Soc. 1999, 121, 8941. (c) Dorigo A. E.; Wanner J.; Schleyer, P. V. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 476. (d) Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11025.
19. For theoretical studies on relevant Cu(III) species, see: (a) Nakamura, E.; Yamanaka, M.; Mori, S. J. Am. Chem. Soc. 2000, 122, 1826. (b) Nakamura, E.; Yamanaka, M. J. Am. Chem. Soc. 1999, 121, 8941. (c) Dorigo A. E.; Wanner J.; Schleyer, P. V. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 476. (d) Snyder, J. P. J. Am. Chem. Soc. 1995, 117, 11025.
20. -, has been determined by X-ray crystallography: (a) Hope, H.; Olmstead, M. M.; Power, P. P.; Sandell, J.; Xu, U. X. J. Am. Chem. Soc. 1985, 107, 4337.
21. This species was reported to be unreactive towards simple electrophiles such as 1-dodecanylbromide in the condensed phase: (b) Mori, S.; Nakamura, E.; Morokuma, K. J. Am. Chem. Soc. 2000, 122, 7294.
22. - as well as higher clusters: (a) Lipshutz B. H., Keith J., Buzard D. J. Organometallics 1999, 18, 1571.
23. Other spectroscopic techniques have also shown that a range of species can be present in solution: (b) Xie, X. L.; Auel, C.; Henze, W.; Gschwind, R. M. J. Am. Chem. Soc. 2003, 125, 1595. (c) Gschwind, R. M.; Xie, X. L.; Rajamohanan, P. R.; Auel, C.; Boche, G. J. Am. Chem. Soc. 2001, 123, 7299. (d) John, M.; Auel, C.; Behrens, C.; Marsch, M.; Harms, K.; Bosold, F.; Gschwind, R. M.; Rajamohanan, P. R.; Boche, G. Chem. Eur. J. 2000, 6, 3060. (e) Huang, H.; Liang, C. H.; Penner-Hahn, J. E. Angew. Chem., Int. Ed. 1998, 37, 1564. (f) Gerold, A.; Jastrzebski J. T. B. H.; Kronenburg, C. M. P.; Krause, N. van Koten, G. Angew. Chem., Int. Ed. 1997, 36, 755.
24. Other spectroscopic techniques have also shown that a range of species can be present in solution: (b) Xie, X. L.; Auel, C.; Henze, W.; Gschwind, R. M. J. Am. Chem. Soc. 2003, 125, 1595. (c) Gschwind, R. M.; Xie, X. L.; Rajamohanan, P. R.; Auel, C.; Boche, G. J. Am. Chem. Soc. 2001, 123, 7299. (d) John, M.; Auel, C.; Behrens, C.; Marsch, M.; Harms, K.; Bosold, F.; Gschwind, R. M.; Rajamohanan, P. R.; Boche, G. Chem. Eur. J. 2000, 6, 3060. (e) Huang, H.; Liang, C. H.; Penner-Hahn, J. E. Angew. Chem., Int. Ed. 1998, 37, 1564. (f) Gerold, A.; Jastrzebski J. T. B. H.; Kronenburg, C. M. P.; Krause, N. van Koten, G. Angew. Chem., Int. Ed. 1997, 36, 755.
25. Other spectroscopic techniques have also shown that a range of species can be present in solution: (b) Xie, X. L.; Auel, C.; Henze, W.; Gschwind, R. M. J. Am. Chem. Soc. 2003, 125, 1595. (c) Gschwind, R. M.; Xie, X. L.; Rajamohanan, P. R.; Auel, C.; Boche, G. J. Am. Chem. Soc. 2001, 123, 7299. (d) John, M.; Auel, C.; Behrens, C.; Marsch, M.; Harms, K.; Bosold, F.; Gschwind, R. M.; Rajamohanan, P. R.; Boche, G. Chem. Eur. J. 2000, 6, 3060. (e) Huang, H.; Liang, C. H.; Penner-Hahn, J. E. Angew. Chem., Int. Ed. 1998, 37, 1564. (f) Gerold, A.; Jastrzebski J. T. B. H.; Kronenburg, C. M. P.; Krause, N. van Koten, G. Angew. Chem., Int. Ed. 1997, 36, 755.
26. Other spectroscopic techniques have also shown that a range of species can be present in solution: (b) Xie, X. L.; Auel, C.; Henze, W.; Gschwind, R. M. J. Am. Chem. Soc. 2003, 125, 1595. (c) Gschwind, R. M.; Xie, X. L.; Rajamohanan, P. R.; Auel, C.; Boche, G. J. Am. Chem. Soc. 2001, 123, 7299. (d) John, M.; Auel, C.; Behrens, C.; Marsch, M.; Harms, K.; Bosold, F.; Gschwind, R. M.; Rajamohanan, P. R.; Boche, G. Chem. Eur. J. 2000, 6, 3060. (e) Huang, H.; Liang, C. H.; Penner-Hahn, J. E. Angew. Chem., Int. Ed. 1998, 37, 1564. (f) Gerold, A.; Jastrzebski J. T. B. H.; Kronenburg, C. M. P.; Krause, N. van Koten, G. Angew. Chem., Int. Ed. 1997, 36, 755.
27. Other spectroscopic techniques have also shown that a range of species can be present in solution: (b) Xie, X. L.; Auel, C.; Henze, W.; Gschwind, R. M. J. Am. Chem. Soc. 2003, 125, 1595. (c) Gschwind, R. M.; Xie, X. L.; Rajamohanan, P. R.; Auel, C.; Boche, G. J. Am. Chem. Soc. 2001, 123, 7299. (d) John, M.; Auel, C.; Behrens, C.; Marsch, M.; Harms, K.; Bosold, F.; Gschwind, R. M.; Rajamohanan, P. R.; Boche, G. Chem. Eur. J. 2000, 6, 3060. (e) Huang, H.; Liang, C. H.; Penner-Hahn, J. E. Angew. Chem., Int. Ed. 1998, 37, 1564. (f) Gerold, A.; Jastrzebski J. T. B. H.; Kronenburg, C. M. P.; Krause, N. van Koten, G. Angew. Chem., Int. Ed. 1997, 36, 755.
28. Isotope labeling studies: (a) Komiya, S.; Albright, T. A.; Hoffmann, R.; Kochi, J. K. J. Am. Chem. Soc. 1976, 98, 7255. (b) Guo, C. Y.; Brownawell, M. L.; San Filippo, J. J. Am. Chem. Soc. 1985, 107, 6028.
29. Isotope labeling studies: (a) Komiya, S.; Albright, T. A.; Hoffmann, R.; Kochi, J. K. J. Am. Chem. Soc. 1976, 98, 7255. (b) Guo, C. Y.; Brownawell, M. L.; San Filippo, J. J. Am. Chem. Soc. 1985, 107, 6028.
30. Gilman was the first to show that PhAg is less reactive than PhCu: Gilman, H.; Straley, J. M., Recl. Trav. Chim. Pay-Bas. 1936, 55, 821.
31. For other examples of organosilver species reacting more selectively than organocopper species: (b) Westmijze, H.; Kleijn, H.; Vermeer P. J. Organomet. Chem. 1979, 172, 377. (c) Kleijn, H.; Westmijze, H.; Meijer, J.; Vermeer P. J. Organomet. Chem. 1981, 206, 257.
32. For other examples of organosilver species reacting more selectively than organocopper species: (b) Westmijze, H.; Kleijn, H.; Vermeer P. J. Organomet. Chem. 1979, 172, 377. (c) Kleijn, H.; Westmijze, H.; Meijer, J.; Vermeer P. J. Organomet. Chem. 1981, 206, 257.
33. The nature of metal catalysts can influence the coupling of Grignard reagents with organic halides. Silver catalysts facilitate homocoupling, while copper catalysts prefer cross coupling: Kochi, J. K. J. Organomet. Chem. 2002, 653, 11 and refs cited therein.
34. -1, a spray voltage of 4.0-5.0 kV, a capillary temperature of 200°C, a nitrogen sheath pressure of 40 psi, and capillary and tube lens offset voltage in the range of -30 to -20 V. The major isotope ions of Cu or Ag were mass selected (with a 1.5 Th window) and subjected to CID: activation amplitude, 0.55-0.65 V; activation (Q), 0.25 V; and activation time 30 ms. Work by Gronert has shown that the ions in a LCQ QIT are essentially at room temperature: (b) Gronert, S. J. Am. Soc. Mass Spectrom. 1998, 9, 845.
35. -1, a spray voltage of 4.0-5.0 kV, a capillary temperature of 200°C, a nitrogen sheath pressure of 40 psi, and capillary and tube lens offset voltage in the range of -30 to -20 V. The major isotope ions of Cu or Ag were mass selected (with a 1.5 Th window) and subjected to CID: activation amplitude, 0.55-0.65 V; activation (Q), 0.25 V; and activation time 30 ms. Work by Gronert has shown that the ions in a LCQ QIT are essentially at room temperature: (b) Gronert, S. J. Am. Soc. Mass Spectrom. 1998, 9, 845.
36. Optimizations and frequency and IRC calculations were carried out at the MP2/6-31++G** level of theory, using the ECPs for Cu (SVP), Ag (SSD), and I (SSD). Data are given in Supporting Information. The MP2 level of theory has been used since it gives a closer match to experimental bond lengths than the B3LYP method: Yamanaka, M.; Inagaki, A. Nakamura, E. J. Comput. Chem. 2003, 24, 1401. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
37. Optimizations and frequency and IRC calculations were carried out at the MP2/6-31++G** level of theory, using the ECPs for Cu (SVP), Ag (SSD), and I (SSD). Data are given in Supporting Information. The MP2 level of theory has been used since it gives a closer match to experimental bond lengths than the B3LYP method: Yamanaka, M.; Inagaki, A. Nakamura, E. J. Comput. Chem. 2003, 24, 1401. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
38. O'Hair, R. A. J Chem. Commun. 2002, 20.
39. Decarboxylation reactions have been used to synthesize organometallics in the condensed phase: (a) Deacon, G. B.; Faulks, S. J.; Pain, G. N. Adv. Organomet. Chem. 1986, 25, 237. Copper(I) salts can catalyze the decomposition of carboxylic acids, but the mechanism of these catalytic reactions are quite complex and may not involve organometallic intermediates: (b) Darensbourg, D. J.; Holtcamp, M. W.; Longridge, E. M.; Khandelwal, B.; Klausmeyer, K. K.; Reibenspies, J. H. J. Am. Chem. Soc. 1995, 117, 318. (c) Darensbourg, D. J.: Holtcamp, M. W.; Khandelwal, B.; Klausmeyer, K. K.; Reibenspies, J. H. Inorg. Chem. 1995, 34, 2389
40. Decarboxylation reactions have been used to synthesize organometallics in the condensed phase: (a) Deacon, G. B.; Faulks, S. J.; Pain, G. N. Adv. Organomet. Chem. 1986, 25, 237. Copper(I) salts can catalyze the decomposition of carboxylic acids, but the mechanism of these catalytic reactions are quite complex and may not involve organometallic intermediates: (b) Darensbourg, D. J.; Holtcamp, M. W.; Longridge, E. M.; Khandelwal, B.; Klausmeyer, K. K.; Reibenspies, J. H. J. Am. Chem. Soc. 1995, 117, 318. (c) Darensbourg, D. J.: Holtcamp, M. W.; Khandelwal, B.; Klausmeyer, K. K.; Reibenspies, J. H. Inorg. Chem. 1995, 34, 2389
41. Decarboxylation reactions have been used to synthesize organometallics in the condensed phase: (a) Deacon, G. B.; Faulks, S. J.; Pain, G. N. Adv. Organomet. Chem. 1986, 25, 237. Copper(I) salts can catalyze the decomposition of carboxylic acids, but the mechanism of these catalytic reactions are quite complex and may not involve organometallic intermediates: (b) Darensbourg, D. J.; Holtcamp, M. W.; Longridge, E. M.; Khandelwal, B.; Klausmeyer, K. K.; Reibenspies, J. H. J. Am. Chem. Soc. 1995, 117, 318. (c) Darensbourg, D. J.: Holtcamp, M. W.; Khandelwal, B.; Klausmeyer, K. K.; Reibenspies, J. H. Inorg. Chem. 1995, 34, 2389
42. 2 into organocopper species, has been described: Mankad, N. P.; Gray, T. G.; Laitar, D. S.; Sadighi, J. P.; Organometallics 2004, 23, 1191
43. Cu(II) organometallics have been implicated: Navon, N.; Golub G.; Cohen, H.; Meyerstein, D., Organometallics 1995, 14, 5670.
44. Reaction efficiencies were calculated using: Chesnavich, W. J.; Su, T.; Bowers, M. T. J. Chem. Phys. 1980, 72, 2641
45. (a) O'Hair, R. A. J.; Davico, G. E.; Hacaloglu, J.; Dang, T. T.; DePuy, C. H.; Bierbaum, V. M., J. Am. Chem. Soc. 1994, 116, 3609.
46. (b) Hosteller, M. J.; Bergman, R. G., J. Am. Chem. Soc. 1992, 114, 7629.
47. 3Cu)] complex instead. A comprehensive manual search failed to find a T-shaped Cu intermediate without any imaginary frequencies.