Gas-phase study on the C-C coupling of naphthol catalyzed by Ci II ·TMEDA: Evidence for the key role of binuclear clusters

Chemistry - A European Journal

Volumn 14, Issue 7, 2008, Pages 2180-2188

  Roithová, Jana ^a,b   Schröder, Detlef ^b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

C C coupling; Copper; Gas phase reactions; Mass spectrometry; Reaction mechanisms

Indexed keywords

COPPER;

BINAPHTHOL; C - C COUPLINGS; C-C COUPLING; COU PLING REACTIONS; GAS-PHASE; GAS-PHASE REACTIONS; MASS SPECTROMETRY; MODEL SYSTEMS; OXIDATIVE COUPLINGS; REACTION MECHANISMS; TETRAMETHYL ETHYLENEDIAMINE;

PHENOLS;

CARBON; COPPER; ETHYLENEDIAMINE DERIVATIVE; LIGAND; N,N,N',N' TETRAMETHYLETHYLENEDIAMINE; N,N,N',N'-TETRAMETHYLETHYLENEDIAMINE; NAPHTHOL DERIVATIVE; ORGANOMETALLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; GAS; SYNTHESIS;

CARBON; CATALYSIS; COPPER; ETHYLENEDIAMINES; GASES; LIGANDS; MOLECULAR STRUCTURE; NAPHTHOLS; ORGANOMETALLIC COMPOUNDS;

EID: 42649090001     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200701277     Document Type: Article

References (62)

1. G. Bringmann, A. J. Price Mortimer, P. A. Keller, M. J. Bresser, J. Garner, M. Breuning, Angew. Chem. 2005, 117, 5621;
2. Angew. Chem. Int. Ed. 2005, 44, 5485, and references therein.
3. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174, and references therein.
4. D. R. Stuart, K. Fagnou, Science 2007, 316, 1172.
5. R. Noyori, I. Tomino, Y. Tanimoto, J. Am. Chem. Soc. 1979, 101, 3129.
6. J. M. Brunel, Chem. Rev. 2005, 105, 857, and references therein.
7. Y. Chen, S. Yekta, A. K. Yudin, Chem. Rev. 2003, 103, 3155, and references therein.
8. P. Kočovský. Š. Vyskočil, M. Smrčina, Chem. Rev. 2003, 103, 3213, and references therein.
9. B. Feringa, H. Wynberg, Tetrahedron Lett. 1977, 18, 4447.
10. R. Pummerer, E. Prell, A. Rieche, Ber. Dtsch. Chem. Ges. 1926, 59, 2159.
11. K. Yamamoto, H. Fukishima, Y. Okamoto, K. Hatada, M. Nakazaki, J. Chem. Soc. Chem. Commun. 1984, 1111.
12. a) S.-W. Hon, C.-H. Li, J.-H. Kuo, N. G. Barhale, Y.-H. Liu, Y. Wang, C.-T. Chen, Org. Lett. 2001, 3, 869;
13. b) C.-Y. Chu, D.-R. Hwang, S.-K. Wang, B. J. Uang. Chem. Commun. 2001, 980;
14. c) Z. Luo, Q. Liu, L. Gong, X. Cui, A. Mi, Y. Jiang, Chem. Commun. 2002, 914.
15. J. Doussot, A. Guy, C. Ferroud. Tetrahedron Lett. 2000, 41, 2535.
16. a) M. Matsushita, K. Kamata, K. Yamaguchi, N. Mizuno, J. Am. Chem. Soc. 2005, 127, 6632;
17. b) S. Y. Zhang, J. B. Lan, X. Y. Su, S. J. Guo, L. Chen, J. S. You, R. G. Xie, J. Chem. Res. 2005, 418.
18. J. Jacques, C. Fouquey, Org. Synth. 1988, 67, 1.
19. B. E. Love, Curr. Org. Synth. 2006, 3, 169.
20. J. Brussee, A. C. Jansen, Tetrahedron Lett. 1983, 24, 3261.
21. M. C. Kozlowski, X. Li, P. J. Carroll, Z. Xu, Organometallics 2002, 21, 4513.
22. X. Li, J. B. Hewgley, C. A. Mulrooney, J. Yang, M. C. Kozlowski, J. Org. Chem. 2003, 68, 5500.
23. M. Smrčina, J. Poláková, Š. Vyskočil, P. Kočovský, J. Org. Chem. 1993, 58, 4534.
24. T. Temma, B. Hatano, S. Habaue, Tetrahedron 2006, 62, 8559, and references therein.
25. H. Somei, Y. Asano, T. Yoshida, S. Takizawa, H. Yamataka, H. Sasai, Tetrahedron Lett. 2004, 45, 1841.
26. Z. Luo, Q. Liu, L. Gong, X. Cui, A. Mi, Y. Jiang, Angew. Chem. 2002, 114, 4714;
27. Angew. Chem. Int. Ed. 2002, 41, 4532.
28. J. Gao, J. H. Reibenspies, A. E. Marlell, Angew. Chem. 2003, 115, 6190;
29. Angew. Chem. Int. Ed. 2003, 42, 6008.
30. M. Smrčina, Š. Vyskočil, B. Máca, M. Polášek, T. A. Claxton, A. P. Abbott, P. Kočovský, J. Org. Chem. 1994, 59, 2156.
31. E. Evangelio, D. Ruiz-Molina, Eur. J. Inorg. Chem. 2005, 15, 2957.
32. Y. Jean, A. Liedos, J. K. Burden, R. Hoffmann, J. Am. Chem. Soc. 1988, 110, 4506.
33. W. Kaim, M. Wanner, A. Knödler, S. Záliš, Inorg. Chim. Acta 2002, 337, 163.
34. S. Habaue, R. Muraoka, A. Aikawa, S. Murakami, H. Higashimura, J. Polym. Sci. A 43, 2005, 1635.
35. a) J. Anekwe, A. Hammerschmidl, A. Rompei, B. Krebs, Z. Anorg. Allg. Chem. 2006, 632, 1057;
36. b) J. Reim, B. Krebs, J. Chem. Soc. Dalton Trans. 1997, 3793.
37. M. Hovorka, J. Závada, Tetrahedron 1992, 48, 9517.
38. a) M. Noji, M. Nakajima, K. Koga, Tetrahedron Lett. 1994, 35, 7983;
39. b) M. Nakajima, I. Miyoshi, K. Kanayama, S. Hashimoto, N. Masahiro, K. Koga, J. Org. Chem. 1999, 64, 2264.
40. X. Li, J. Yang, M. C. Kozlowski, Org. Lett. 2001, 3, 1137.
41. J. Roithová, D. Schröder, Phys. Chem. Chem. Phys., 2007, 9, 713.
42. J. Roithová, D. Schröder, J. Míšek, I. G. Stará, I. Starý, J. Mass Spectrom., 2007, 42, 1233.
43. P. Chen, Angew. Chem. 2003, 115, 2938;
44. Angew. Chem. Int. Ed. 2003, 42, 2832.
45. For earlier studies on gas-phase reactions of transition-metal ions with phenol and related compounds, see: a) A. Bjarnason, J. W. Taylor, Organometallics 1990, 9, 1493;
46. b) D. Schröder, W. Zummack, H. Schwarz, Organometallics 1993, 12, 1079;
47. c) J. M. Carreteas, A. P. de Matos, J. Marcalo, J. Am. Soc. Mass Spectrom. 1998, 9, 1035;
48. d) V. Ryzhov, R. C. Dunbar, J. Am. Chem. Soc. 1999, 121, 2259;
49. e) M. Brönstrup, D. Schröder, H. Schwarz, Chem. Eur. J. 2000, 6, 91;
50. f) I. Corral, O. Mo., M. Yañez, Int. J. Mass Spectrom. 2006, 255, 20.
51. E. Zocher, R. Dietiker, P. Chen, J. Am. Chem. Soc. 2007, 129, 2476.
52. N. G. Tsierkezos, D. Schröder, H. Schwarz, Int. J. Mass Spectrom. 2004, 235, 33.
53. K. M. Stirk, J. C. Orlowski, D. T. Leeck, H. I. Kenttämaa, J. Am. Chem. Soc. 1992, 114, 8604.
54. 3S. abstraction is observed too.
55. +.
56. + complex is impossible, because the latter is not formed in an amount sufficient to allow CID experiments with the mass-selected ion.
57. For similar rapid consecutive eliminations of two neutral entities from gaseous ions, see: a) D. Schröder, H. Schwarz, J. Am. Chem. Soc. 1990, 112, 5947;
58. b) D. Schröder, J. Roithová, P. Gruene, H. Schwarz, H. Mayr, K. Koszinowski, J. Phys. Chem. A 2007, 111, 8925.
59. Keto/enol rearrangements are generally assumed to be facile processes which are enabled by general acid/base catalysis in protic solvents. In the gas phase or aprotic solvents, however, 1,3-H transfers are anything but facile; see also: C. Trage, D. Schröder, H. Schwarz, Chem. Eur. J. 2005, 11, 619.
60. N. Kitajima, Y. Moro-oka, Chem. Rev. 1994, 94, 737.
61. We note that monodentate nitrogen bases also support clustering of copper. For example, see: a) R. Kurtaran, L. T. Yildirim, A. D. Azaz, H. Namli, O. Atakol, J. Inorg. Biochem. 2005, 99, 1937;
62. b) N. G. Tsierkezos, J. Roithová, D. Schröder, I. E. Molinou, H. Schwarz, unpublished results.