Palladacycle as highly efficient catalyst for ring opening of oxabicyclic alkenes with organozinc halides

Journal of Organometallic Chemistry

Volumn 692, Issue 10, 2007, Pages 1912-1919

  Zhang, Ting Ke ^a   Yuan, Ke ^a   Hou, Xue Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

C C bond formation; Organozinc halides; Oxabicyclic alkene; Palladacycle; Palladium; Ring opening reaction

Indexed keywords

BOND STRENGTH (CHEMICAL); CATALYSIS; CATALYSTS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLICS; PALLADIUM; RING OPENING POLYMERIZATION;

BOND FORMATION; CATALYST PRECURSOR; ORGANOZINC HALIDES; OXABICYCLIC ALKENE; PALLADACYCLE;

OLEFINS;

EID: 33947595460     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2006.12.039     Document Type: Article

References (70)

1. In: Negishi E.-I., and de Meijere A. (Eds). Handbook of Organopalladium Chemistry for Organic Synthesis (2002), Wiley, New York
2. For review:. Herrmann W.A., Böhm V.P.W., and Reisinger C.-P. J. Organomet. Chem. 576 (1999) 23
3. Dupont J., Pfeiffer M., and Spencer J. Eur. J. Inorg. Chem. (2001) 1917
4. Bedford R.B. Chem. Commun. (2003) 1787
5. Farina V. Adv. Synth. Cat. 346 (2004) 1553
6. Beletskaya I.P., and Cheprakov A.V. J. Organomet. Chem. 689 (2004) 4055
7. Dupont J., Consorti C.S., and Spencer J. Chem. Rev. 105 (2005) 2527
8. Herrmann W.A., Brossmer C., Ofele K., Reisinger C.-P., Priermeier T., Beller M., and Fischer H. Angew. Chem., Int. Ed. Engl. 34 (1995) 1844
9. Some examples of palladacycles in Heck reaction and coupling reactions:. Ohff M., Ohff A., Boom M.E., and Milstein D. J. Am. Chem. Soc. 119 (1997) 11687
10. Shaw B.L., Perera S.D., and Staley E.A. Chem. Commun. (1998) 1361
11. Ohff M., Ohff A., and Milstein D. Chem. Commun. (1999) 357
12. Gruber A.S., Zim D., Ebeling G., Monteiro A.L., and Dupont J. Org. Lett. 2 (2000) 1287
13. Wu Y., Hou J., Yun H., Cui X., and Yuan Y. J. Organomet. Chem. 637-639 (2001) 793
14. Alonso D.A., Nájera C., and Pacheco M.C. Adv. Synth. Catal. 344 (2002) 172
15. Botella L., and Nájera C. Angew. Chem., Int. Ed. 42 (2002) 179
16. Iyer S., Kulkarni G.M., and Ramesh C. Tetrahedron 60 (2004) 2163
17. Svennebring A., Nilsson P., and Larhed M. J. Org. Chem. 69 (2004) 3345
18. Liang B., Dai M., Chen J., and Yang Z. J. Org. Chem. 70 (2005) 391
19. Zhang J., Zhao L., Song M., Mak T.C.W., and Wu Y. J. Organomet. Chem. 691 (2006) 1301
20. Yang F., Zhang Y., Zheng R., Tang J., and He M. J. Organomet. Chem. 651 (2002) 146
21. Navarro O., Marion N., Oonishi Y., Kelly III R.A., and Nolan S.P. J. Org. Chem. 71 (2006) 685
22. Some examples of palladacycles used in other reactions:. Calter M., Hollis T.K., Overman L.E., Ziller J., and Zipp G.G. J. Org. Chem. 62 (1997) 1449
23. Donde Y., and Overman L.E. J. Am. Chem. Soc. 121 (1999) 2933
24. Overman L.E., and Remarchuk T.P. J. Am. Chem. Soc. 124 (2002) 12
25. Moyano A., Rosol M., Moreno R.M., López C., and Maestro M.A. Angew. Chem., Int. Ed. 44 (2005) 1865
26. Anderson C.E., Donde Y., Douglas C.J., and Overman L.E. J. Org. Chem. 70 (2005) 648 and references cited therein.
27. Weiss M.E., Fischer D.F., Xin Z.-q., Jautze S., Schweizer W.B., and Peters R. Angew. Chem. Int. Ed. 45 (2006) 5694
28. Brunel J.M., Heumann A., and Buono G. Angew. Chem., Int. Ed. 39 (2000) 1946
29. Louis J., and Hartwig J.F. Angew. Chem., Int. Ed.Engl. 34 (1996) 2359
30. Nowotny M., Hanefeld U., van Koningsveld H., and Maschmeyer T. Chem. Commun. (2000) 1877
31. Brody M.S., and Finn M.G. Tetrahedron Lett. 40 (1999) 415
32. Tietze L.F., Schirok H., Wöhrmann M., and Scherader K. Eur. J. Org. Chem. (2000) 2433
33. For reviews, see:. Chiu P., and Lautens M. Top. Curr. Chem. 190 (1997) 1
34. Lautens M. Synlett (1993) 177
35. Lautens M., Fagnou K., and Hiebert S. Acc. Chem. Res. 36 (2003) 48
36. For some recent papers:. Millward D.B., Sammis G., and Waymouth R.M. J. Org. Chem. 65 (2000) 3902
37. Priego J., Mancheno O.G., Cabrera S.C., Arrayas R.G., Llamas T., and Carretero J.C. Chem. Commun. (2002) 2512
38. Rayabarapu D.K., Chiou C.-F., and Cheng C.-H. Org. Lett. 4 (2002) 1679
39. Murakami M., and Igawa H. Chem. Commun. (2002) 390
40. Bertozzi F., Pineschi M., Macchia F., Arnold L.A., Minnaard A.J., and Feringa B.L. Org. Lett. 4 (2002) 2703
41. Lautens M., Dockendorff C., Fagnou K., and Malicki A. Org. Lett. 4 (2002) 1311
42. Lautens M., and Dockendorff C. Org. Lett. 5 (2003) 3695
43. Arrayás R.G., Cabrera S., and Carretero J.C. Org. Lett. 5 (2003) 1333
44. Li L.-P., Rayabarapu D.K., Nandi M., and Cheng C.-H. Org. Lett. 5 (2003) 1621
45. Nakamura M., Matsuo K., Inoue T., and Nakamura E. Org. Lett. 5 (2003) 1373
46. Lautens M., and Hiebert S. J. Am. Chem. Soc. 126 (2004) 1437
47. Zhang W., Wang L.-X., Shi W.-J., and Zhou Q.-L. J. Org. Chem. 70 (2005) 3734
48. Cabrera S., Arrayás R.G., Alonso I., and Carretero J.C. J. Am. Chem. Soc. 127 (2005) 13938
49. Imamoto T., Sugitu K., and Yoshida K. J. Am. Chem. Soc. 127 (2005) 11934
50. Chen C.-L., and Martin S.F. J. Org. Chem. 71 (2006) 4810
51. Lautens showed an example using 0.05 mol% of cationic Pd-complex in reaction, see Ref. [9k].
52. Dai L.-X., Tu T., You S.-L., Deng W.-P., and Hou X.-L. Acc. Chem. Res. 36 (2003) 659
53. Hou X.-L., You S.-L., Tu T., Deng W.-P., Wu X.-W., Li M., Yuan K., Zhang T.Z., and Dai L.-X. Top. Catal. 35 (2005) 87
54. Hou X.-L., and Sun N. Org. Lett. 6 (2004) 4399 Corrections: Org. Lett. 2005, 7, 1435
55. Li M., Yan X.-X., Hong W., Zhu X.-Z., Cao B.-X., Sun J., and Hou X.-L. Org. Lett. 6 (2004) 2833
56. Yan X.-X., Liang C.-G., Zhang Y., Hong W., Cao B.-X., Dai L.-X., and Hou X.-L. Angew. Chem., Int. Ed. 44 (2005) 6544
57. Zheng W.-H., Sun N., and Hou X.-L. Org. Lett. 7 (2005) 5151
58. Yan X.-X., Peng Q., Zhang Y., Zhang K., Hong W., Hou X.-L., and Wu Y.-D. Angew. Chem., Int. Ed. 45 (2006) 1979
59. Yuan K., Zhang T.-K., and Hou X.-L. J. Org. Chem. 70 (2005) 6085
60. Hosokawa T., Uno T., Inui S., and Murahashi S.-I. J. Am. Chem. Soc. 103 (1981) 2318
61. Hosokawa T., Okuda C., and Murahashi S.-I. J. Org. Chem. 60 (1995) 2648
62. Gavina F., Luis S.V., and Costero A.M. Tetrahedron 42 (1986) 155
63. Anthony I.J., and Wege D. Aust. J. Chem. 49 (1996) 1263
64. Jung K.-Y., and Koreeda M. J. Org. Chem. 54 (1989) 5667
65. Schlueter A.-D., Belzner J., Heywang U., and Szeimies G. Tetrahedron Lett. 24 (1983) 891
66. Rivera J.M., Martin T., and Rebek Jr. J. J. Am. Chem. Soc. 123 (2001) 5213
67. Gillet J.P., Sauvetre R., and Normant J.F. Synthesis (1986) 538
68. Coulsen D.R. Inorg. Synth. 13 (1972) 121
69. Lautens M., Renaud J., and Hiebert S. J. Am. Chem. Soc. 122 (2000) 1804
70. Seinosuke O., Akira N., Tosizi K., and Kazuhide T. J. Am. Chem. Soc. 93 (1971) 4301