FeCp+ induced heterolytic cleavage of phenyl ethers and transetherification

New Journal of Chemistry

Volumn 20, Issue 10, 1996, Pages 1071-1080

  Djakovitch, Laurent ^a   Moulines, Françoise ^a   Astruc, Didier ^a  

^a CNRS   (France)

Author keywords

Activation by FeCp+; Aromatic complexes; Ether cleavage

Indexed keywords

EID: 0000344845     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (96)

1. 3).
2. Elschenbroich C., Salzer A., Organometallics. A Concise Introduction, 2nd ed., VCH, Weinheim, 1992, Chap. 15 (Activation by Various Metals).
3. 3 activation).
4. 2+ complexes, see ref. 16).
5. Pearson A. J., Metallo-Organic Chemistry, Wiley, 1985, New York (many pioneering examples with various metals).
6. Trahanovsky W. S., Card R. J., J. Am. Chem. Soc., 1972, 94, 2837.
7. For seminal studies, see Semmelhack N.Y. Acad. Sci., 1977, 295, 36;
8. Pure Appl. Chem., 1981, 53, 2379.
9. Brookhart M., Lamanna W., Pinhas A. R., Organometallics, 1983, 2, 638;
10. Lamanna W., Brookhart M., J. Am. Chem. Soc., 1981, 103, 989;
11. Lamanna W., Brookhart M., J. Am. Chem. Soc., 1982, 104, 2117;
12. Brookhart M., Lukacs A., J. Am. Chem. Soc., 1984, 106, 4161.
13. Chung Y. K., Sweigart D. A., Connelly N. G., Sheridan J. B., J. Am. Chem. Soc., 1985, 107, 2388.
14. Pearson A. J., Bruhn P. R., Gonzoules F., Lee S. H., J. Chem. Soc., Chem. Commun., 1989, 659.
15. a) Djukic J. P., Rose-Munch F., Rose E., J. Chem. Soc., 1993, 115, 6434;
16. b) Balssa F., Aniss K., Rose-Munch F., Tetrahedron Lett., 1992, 31, 1901.
17. Weber S. R., Brintzinger H. H., J. Organomet. Chem., 1977, 127, 45.
18. Cameron T. S., Clerck M. D., Linden A., Stunge K., Zaworotko M. J., Organometallics, 1988, 7, 2571.
19. a) Madonik A., Astruc D., J. Am. Chem. Soc., 1984, 106, 2437-2439;
20. b) Madonik A., Mandon D., Michaud P., Lapinte C., Astruc D., J. Am. Chem. Soc., 1984, 106, 3381;
21. c) Mandon D., Toupet L., Astruc D., J. Am. Chem. Soc., 1986, 108, 1320.
22. Astruc D., Synlett, 1991, 369 (account).
23. Astruc D., Michaud P., Madonik A. M., Saillard J.-Y., Hoffmann R., Nouv. J. Chim., 1985, 9, 41.
24. Astruc D., Tetrahedron Report no 157, Tetrahedron, 1983, 39, 4027.
25. Astruc D., in The Chemistry of the Metal-Carbon Bond, Hartley FR Ed., Wiley, New York, 1987, 4, 625-731.
26. Hull J. W., Gladfelter W. L., Organometallics, 1982, 1, 1716.
27. Tam W., Vollhardt K. P. C., J. Organomet. Chem., 1981, 216, 97.
28. a) Maitlis P., Acc. Chem. Res., 1978, 11, 301;
29. b) Chem. Soc. Rev., 1981, 10, 1;
30. c) White C., Thomson S. J., Maitlis P. M., J. Chem. Soc., Dalton Trans., 1977, 1654;
31. d) J. Organomet. Chem., 1977, 127, 415.
32. Abd-El-Aziz A. S., Lee C. C., Piorko A., Sutherland R. G., J. Organomet. Chem., 1988, 348, 95 (review).
33. a) Pearson A. J., Park J. G., Yang S. H., Chuang Y. H., J. Chem. Soc., Chem. Commun., 1989, 1363.
34. Astruc D., Top Curr. Chem., 1991, 160, 47.
35. Astruc D., Hamon J. R., Mandon D., Moulines F., Pure Appl. Chem., 1990, 62, 1165.
36. Urbanos F., Halcrow M. A., Fernandez-Baeza J., Dahan F., Labroue D., Chaudret B., J. Am. Chem. Soc., 1993, 115, 3484.
37. Moriarty R. M., Yi-Yin Ku, Crio L., J. Chem. Soc., Chem. Commun., 1988, 1621.
38. Segal J. A., J. Chem. Soc., Chem. Commun., 1985, 1338.
39. +, see ref. 30 and Balas L., Jhurry D., Latxague L., Grelier S., Morel Y., Hamdani M., Ardoin N., Astruc D., Bull. Soc. Chim. Fr., 1990, 127, 401.
40. Kane-Maguire L. A. P., Hong D., Sweigart D. A., Chem. Rev., 1984, 84, 525.
41. 3 activator has been recently reported: see refs. 32 and 33.
42. Kundig E. P., Desobry V., Simmons D. P., Wenger E., J. Am. Chem. Soc., 1989, 111, 1804.
43. Djukic J.-P., Rose-Munch F., Rose E., J. Chem. Soc., Chem. Commun., 1991, 1634.
44. For activation of aromatics by metal monoelectronic oxidation, see Sheldon R. A., Kochi J. K., Metal-Catalyzed Oxidation of Organic Compounds, Academic, New York, 1981.
45. For activation of arenes by oxidative addition of a C-H bond see, for example: Arndtsen B. A., Bergman R. G., Science, 1995, 270, 1970.
46. For activation of arenes by oxidative addition of a C-halogen bond, see Heck R. F., Pure Appl. Chem., 1978, 50, 691.
47. a) Moulines F., Gloaguen B., Astruc D., Angew. Chem., 1992, 452;
48. Angew. Chem. Int. Ed. Engl., 1992, 28, 458,
49. b) Moulines F., Djakovitch L., Boese R., Gloaguen B., Thiel W., Fillaut J.-L., Delville M.-H., Astruc D., Angew. Chem., 1993, 105, 1132-1134;
50. Angew. Chem. Int. Ed. Engl., 1993, 32, 1075-1077;
51. c) Buchholz D., Astruc D., Angew. Chem., 1994, 106, 1721-1722;
52. Angew. Chem. Int. Ed. Engl., 1994, 33, 1637-1639;
53. d) Fillaut J.-L., Linares J., Astruc D., Angew. Chem., 1994, 106, 2540-2542;
54. Angew. Chem. Int. Ed. Engl., 1994, 33, 2460-2462;
55. e) Moulines F., Astruc D., Angew. Chem. Int. Ed. Engl., 1988, 27, 1347-1349;
56. Angew. Chem., 1988, 100, 1394-1396;
57. f) Buchholz D., Gloaguen B., Fillaut J.-L., Cotrait M., Astruc D., Chem. Eur. J., 1995, 1, 374.
58. Moulines F., Djakovitch L., Delville M.-H., Robert F., Gouzerth P., Astruc D., J. Chem. Soc., Chem. Commun., 1995, 463-464.
59. Staude E., Patat F., in The Chemistry of the Ethers Linkage, Patai S., Ed., Wiley, New York, 1967, 46.
60. Maercher A., Angew. Chem., 1987, 99, 1002;
61. Angew. Chem. Int. Ed. Engl., 1987, 26, 972.
62. Buncel E., Dust J. M., Jonczyk A., Manderville R. A., Onyido I., J. Am. Chem. Soc., 1992, 114, 5610.
63. Stoermer R., Kahlert B., Chem. Ber., 1901, 34, 1812.
64. Rose-Munch F., Djukic J. P., Rose E., Tetrahedron Lett., 1990, 31, 2589.
65. Djukic J. P., Rose-Munch F., Rose E., Simon F., Dromzee Y., Organometallics, 1995, 14, 2027.
66. Kimura M., Morita M., Mitani H., Okamoto H., Satake K., Morosawa S., Bull. Soc. Chim. Jpn., 1992, 65, 2557.
67. Cole-Hamilton D. J., Young R. J., Wilkinson G., J. Chem. Soc., Dalton Trans., 1976, 1995.
68. Helling J. F., Hendrickson W. A., J. Organomet. Chem., 1979, 168, 87.
69. Koelle U., Hong Wang M., Raabe G., Organometallics, 1991, 10, 2574.
70. Chaudret B., He X., Huang Y., J. Chem. Soc., Chem. Commun., 1989, 1844.
71. a) El-Amouri H., Gruselle M., Jackson P. A., Jaouen G., Vaisserman J., Organometallics, 1990, 9, 2871;
72. b) Le Bras J., El-Amouri H., Besace Y., Vaissermann J., Jaouen G., Bull. Soc. Chim. Fr., 1995, 132, 1073.
73. Lee S.-G., Kim J.-A., Chung Y. K., Yoon T.-S., Kim N.-J., Shin W., Kim J., Kim K., J. Organomet. Chem., 1995, 14, 1023.
74. Nesmeyanov A. N., Vol'kenau N. A., Bolesova I. N., Dokl. Akad. Nauk SSSR, 1967, 175, 606.
75. Nesmeyanov A. N., Vol'kenau N. A., Isaeva L. S., Bolesova I. N., Dokl. Akad. Nauk SSSR, 1968, 183, 351.
76. a) Lee C. C., Abd-El-Aziz A. S., Chowdhurry R. L., Gill U. S., Piorko A., Sutherland R. G., J. Organomet. Chem., 1986, 315, 79;
77. Lee C. C., Abd-El-Aziz A. S., Chowdhurry R. L., Gill U. S., Piorko A., Sutherland R. G., J. Organomet. Chem., 1990, 395, 293;
78. b) Abd-El-Aziz A. S., De Demus C., J. Chem. Soc., Chem. Commun., 1994, 663;
79. c) Abd-El-Aziz A. S., Schriemer D. C., De Demus C., Organometallics, 1994, 13, 374.
80. a) Djakovitch L., Thesis, Bordeaux, 1995;
81. b) Djakovitch L., Moulines F., Fillaut J.-L., Astruc D., unpublished work.
82. -, see Loupy A., Tchoubar B., Astruc D., Chem. Rev., 1992, 92, 1141.
83. Loupy A., Tchoubar B., Effets de Sels en Chimie Organique et Organométallique, Dunod, Paris, 1988;
84. Salt Effects in Organic and Organomelallic Chemistry, VCH, Weinheim, 1992.
85. Michaud P., Astruc D., Ammeter J. H., J. Am. Chem. Soc., 1982, 104, 3755.
86. Ruiz J., Lacoste M., Astruc D., J. Am. Chem. Soc., 1990, 112, 5471.
87. a) Ref. 67, Chap. 5;
88. b) Ref. 67, Chap. 1.
89. For the structure and reactivity of triple and quadruple ions, see Refs. 60, 61, 67 and Mechanisms and Processes in Molecular Chemistry, Astruc D., Ed. Gauthier-Villars, Paris, New J. Chem., 1992, 16, 1-330.
90. Bock H., Herman H. F. in Ref. 61, p. 29.
91. Casado C. M., Wagner T., Astruc D., J. Organomet. Chem., 1995, 502, 143.
92. For the X-ray crystal structure of the iron complex 12, see Hamon J. R., Astruc D., Roman E., Batail P., Mayerle J. J., J. Am. Chem. Soc., 1981, 103, 2431.
93. Trujillo H. A., Casado C. M;, Astruc D., J. Chem., Soc. Chem. Commun., 1995, 7.
94. For the electrochemistry of organometallic complexes, see ref. 67, Chap. 2.
95. Astruc D., Electron Transfer and Radical Processes in Transition-Metal Chemistry, VCH, New York, 1995.
96. Hugues R. P., Klaui W., Reisch J. W., Müller A., Organometallics, 1985, 4, 1761.