Oxidative demetalation of Fischer alkoxy carbene complexes with stoichiometric pyridine N-oxide and NaBH4-promoted demetalation of Fischer iminocarbene complexes with sulfur and selenium

Journal of Organometallic Chemistry

Volumn 691, Issue 17, 2006, Pages 3679-3692

  Zheng, Zhaoyan ^a   Chen, Jinzhu ^a   Yu, Zhengkun ^a   Han, Xiuwen ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Fischer carbene; Iminocarbene; Pyridine N oxide; Selenium; Sulfur

Indexed keywords

ESTERS; NITROGEN OXIDES; OXIDATION; PYRITES; SELENIUM; STOICHIOMETRY; SULFUR; X RAY CRYSTALLOGRAPHY;

FISCHER CARBENE; IMINOCARBENE; PYRIDINE N-OXIDE; SULFUR;

FISCHER-TROPSCH SYNTHESIS;

EID: 33745892601     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2006.05.021     Document Type: Article

References (81)

1. For selected recent reviews, see:. Barluenga J., Santamaria J., and Tomás M. Chem. Rev. 104 (2004) 2259
2. Herndon J.W. Coord. Chem. Rev. 243 (2003) 3
3. Sierra M.A. Chem. Rev. 100 (2000) 3591
4. Dötz K.H., Jakel C., and Haase W.C. J. Organomet. Chem. 617/618 (2001) 119
5. Barluenga J., Floréz J., and Fañanás F.J. J. Organomet. Chem. 624 (2001) 5
6. de Meijere A., Schirmer H., and Duetsch M. Angew. Chem., Int. Ed. Engl. 39 (2000) 3964
7. Herndon J.W. Tetrahedron 56 (2000) 1257
8. Barluenga J., and Fañanás F.J. Tetrahedron 56 (2000) 4597
9. Aumann R. Eur. J. Org. Chem. 1 (2000) 17
10. Chen J.Z., Yu Z.K., Zheng Z.Y., Gu K.C., Wu S.Z., Zeng F.L., Tan W.Q., Wu X.W., and Xiao W.-J. Organometallics 24 (2005) 302 and references therein
11. Barluenga J., Aznar F., Gutiérrez I., Martín A., García-Granda S., and Llorca-Baragaño M.A. J. Am. Chem. Soc. 122 (2000) 1314
12. Dötz K.H. Angew. Chem., Int. Ed. Engl. 14 (1975) 644
13. Dötz K.H. Angew. Chem., Int. Ed. Engl. 14 (1975) 644
14. Barluenga J., Aznar F., Gutiérrez I., Martín A., García-Granda S., and Llorca-Baragaño M.A. J. Am. Chem. Soc. 122 (2000) 1314
15. Florio S., Perna F.M., Luisi R., Barluenga J., Fañanás F.J., and Rodríguez F. J. Org. Chem. 69 (2004) 9204 and references therein
16. Representative references:. Hegedus L.S. Tetrahedron 53 (1997) 4105
17. Hegedus L.S. Transition metal carbene complexes: photochemical reactions of carbene complexes. In: Abel E.W., Stone F.G.A., and Wilkinson G. (Eds). Comprehensive Organometallic Chemistry II vol. 12 (1995), Pergamon, Oxford 549
18. Gómez-Gallego M., Mancheño M.J., and Sierra M.A. Acc. Chem. Res. 38 (2005) 44
19. Barluenga J., Barrio P., Vicente R., López L.A., and Tomás M. J. Organomet. Chem. 689 (2004) 3793
20. Barluenga J., Aznar F., Martin A., García-Granda S., and Pérez-Carreño E. J. Am. Chem. Soc. 116 (1994) 11191
21. Wulff W.D., Bax B.M., Brandvold T.A., Chan K.S., Gilbert A.M., Hsung R.P., Mitchell J., and Clardy J. Organometallics 13 (1994) 102
22. Ramírz-López P., Sierra M.A., Gómez-Gallego M., Mancheño M.J., and Gornitzka H. Organometallics 22 (2003) 5092
23. Ramírz-López P., Gómez-Gallego M., Mancheño M.J., Sierra M.A., Bilurbina M., and Ricart S. J. Org. Chem. 68 (2003) 3538
24. Gómez-Gallego M., Mancheño M.J., Ramírez P., Piñar C., and Sierra M.A. Tetrahedron 56 (2000) 4893
25. Barluenga J., Granados A., Rodríguez F., Vadecard J., and Fañanás F.J. Tetrahedron Lett. 38 (1997) 6465
26. Selected references see:. Wulff W.D., Bauta W.E., Kaesler R.W., Lankford P.J., Miller R.A., Murray C.K., and Yang D.C. J. Am. Chem. Soc. 112 (1990) 3642
27. Barluenga J., Aznar F., Barluenga S., Fernández M., Martin A., García-Granda S., and Pinera-Nicolas A. Chem. Eur. J. 4 (1998) 2280
28. Vázquez M.A., Reyes L., Miranda R., García J.J., Jiménez-Vázquez H.A., Tamariz J., and Delgado F. Organometallics 24 (2005) 3413
29. For selected recent literatures, see:. Alcaide B., Casarrubias L., Domínguez G., and Sierra M.A. Curr. Org. Chem. 2 (1998) 551
30. Barluenga J., Fernández-Rodríguez M.A., Aguilar E., Fernández-Marí F., Olano B., and Salinas A. Chem. Eur. J. 7 (2001) 3533
31. Merino I., Laxmi Y.R.S., Flórez J., Barluenga J., Ezquerra J., and Pedregal C. J. Org. Chem. 67 (2002) 648
32. Gu K.C., Chen J.Z., Zheng Z.Y., Wu S.Z., Wu X.W., Han X.W., and Yu Z.K. Polyhedron 24 (2005) 173 and references therein
33. Anderson B.A., Wulff W.D., and Rham A. J. Am. Chem. Soc. 115 (1993) 4602
34. Wulff W.D., and Yang D.C. J. Am. Chem. Soc. 105 (1983) 6726
35. Fischer E.O., Walz S., Kneis G., and Kreissl F.R. Chem. Ber. 110 (1977) 1651
36. Fischer E.O., and Plabst D. Chem. Ber. 107 (1974) 3326
37. Casey C.P., Betz S.H., and Burkhardt T.J. Tetrahedron Lett. 14 (1973) 1421
38. Casey C.P., and Burkhardt T.J. J. Am. Chem. Soc. 94 (1972) 6543
39. Barluenga Jr. J., Bernard P.L., and Concellón J.M. Tetrahedron Lett. 35 (1994) 9471
40. Casey C.P., and Neumann M. J. Am. Chem. Soc. 99 (1977) 1651
41. Selected references, see:. Cotton F.A., and Lukehart C.M. J. Am. Chem. Soc. 93 (1971) 2672
42. Erker G., and Sosna F. Organometallics 9 (1990) 1949
43. Quayle P., Rahman S., Ward E.L.M., and Herbert J. Tetrahedron Lett. 35 (1994) 3801
44. Barluenga J., Tomás M., López-Pelegrín J.A., and Rubio E. Tetrahedron Lett. 38 (1997) 3981
45. Ezquerra J., Pedregal C., Merino I., Flórez J., Barluenga J., García-Granda S., and Llorca M.-A. J. Org. Chem. 64 (1999) 6554
46. Barluenga J., Fernández-Rodríguez M.A., and Aguilar E. Org. Lett. 4 (2002) 3659
47. Capriati V., Florio S., Luisi R., Perna F.M., and Barluenga J. J. Org. Chem. 70 (2005) 5852
48. Casey C.P., Burkhardt T.J., Bunnell C.A., and Calabrese J.C. J. Am. Chem. Soc. 99 (1977) 2127
49. Chan K.S., Yeung M.L., Chan W., Wang R., and Mak T.C.W. J. Org. Chem. 60 (1995) 1741
50. Gibert M., Ferrer M., Lluch A.-M., Sanchez-Baeza F., and Messeguer A. J. Org. Chem. 64 (1999) 1591
51. Lluch A.-M., Gibert M., Sánchez-Baeza F., and Messeguer A. Tetrahedron 52 (1996) 3973
52. Casey C.P., Boggs R.A., and Anderson R.L. J. Am. Chem. Soc. 94 (1972) 8947
53. Casey C.P., and Brunsvold W.R. J. Organomet. Chem. 102 (1975) 175
54. Neidlein R., and Gurtler S. Synthesis (1995) 325
55. Lukehart C.M., and Zeile J.V. J. Organomet. Chem. 97 (1975) 421
56. Aumann R., Schroeder J., and Heinen H. Chem. Ber. 123 (1990) 1369
57. Licandro E., Maiorana S., Papagni A., Hellier P., Capella L., Persoons A., and Houbrechts S. J. Organomet. Chem. 583 (1999) 111
58. Barluenga J., Andina F., Fernández-Rodríguez M.A., Garcia-García P., Merino I., and Aguilar E. J. Org. Chem. 69 (2004) 7352
59. Perdicchia D., Licandro E., Maiorana S., Vandoni B., and Baldoli C. Org. Lett. 4 (2002) 827
60. Dötz K.H., Fügen-Köster B., and Neugebauer D. J. Organomet. Chem. 182 (1979) 489
61. Beddoes R.L., Painter J.E., and Quayle P. Tetrahedron Lett. 37 (1996) 9385
62. Barluenga J., Ballesteros A., de la Rúa R.B., Santamaría J., Rubio E., and Tomás M. J. Am. Chem. Soc. 125 (2003) 1834
63. Aumann R., Yu Z.K., and Fröhlich R. Organometallics 17 (1998) 2897
64. Fischer E.O., and Riedmüller S. Chem. Ber. 107 (1974) 915
65. Shah A.R., Padma D.K., and Murthy A.R.V. Indian J. Chem. 9 (1971) 885
66. Selected literatures, see:. Couture A., Grandclaudon P., and Huguerre E. Synthesis (1989) 456
67. Fischer H., Treier K., and Troll C. Chem. Ber. 128 (1995) 883
68. Bunnelle W.H., Mckinnis B.R., and Narayanan B.A. J. Org. Chem. 55 (1990) 768
69. Murai T., Ogino Y., Mizutani T., Kanda T., and Kato S. J. Org. Chem. 60 (1995) 2942
70. Barton D.H.R., Hansen P.-E., and Picker K. J. Chem. Soc. Perkin I (1977) 1723
71. Fischer E.O., and Kreissl F.R. J. Organoment. Chem. 35 (1972) C47
72. Aumann R., and Heinen H. Chem. Ber. 120 (1987) 537
73. Aumann R., and Fischer E.O. Angew. Chem., Int. Ed. Engl. 6 (1967) 879
74. Darensbourg M.Y., and Darensbourg D.J. Inorg. Chem. 9 (1970) 32
75. Kang S.K., Yoon S.K., and Kim Y.M. Org. Lett. 3 (2001) 2697
76. Balasubramaniyan V., Bhatia G., and Wagh S.B. Tetrahedron 39 (1983) 1475
77. Lewis F.D., Howard D.K., Barancyk S.V., and Oxman J.D. J. Am. Chem. Soc. 108 (1986) 3016
78. Lewis F.D., Howard D.K., Oxman J.D., Upthagrove A.L., and Quillen S.L. J. Am. Chem. Soc. 108 (1986) 5964
79. Shi Z.J., and He C. J. Org. Chem. 69 (2004) 3669
80. Tao W.J., Nesbitt S., and Heck R.F. J. Org. Chem. 55 (1990) 63
81. Dai M.J., Liang B., Wang C.H., Chen J.H., and Yang Z. Org. Lett. 6 (2004) 221