Aerobic dehydrogenative heck reaction of ferrocene with a Pd(OAc) 2/4,5-diazafluoren-9-one catalyst

Organometallics

Volumn 32, Issue 20, 2013, Pages 5709-5712

  Piotrowicz, Michał ^a   Zakrzewski, Janusz ^a  

^a UNIVERSITY OF LODZ   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

FERROCENES; HECK ALKENYLATION; HECK REACTIONS; ROOM TEMPERATURE;

ATMOSPHERIC PRESSURE; HYDROCARBONS;

ORGANOMETALLICS;

EID: 84887058527     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om400410u     Document Type: Article

References (67)

1. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215-1292
2. Kuhl, N.; Hopkinson, M. N.; Wenzel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236-10254
3. Scheuermann, C. J. Chem. Asian J. 2009, 5, 436-451
4. Lyons, T. L.; Sanford, M. Chem. Rev. 2010, 110, 1147-1169
5. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788-802
6. Chen, X.; Engle, K. M.; Wang, D. H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094-5115
7. Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318-5365
8. Ackermann, L.; Vincent, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792-9826
9. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780-1824
10. You, D. G.; Li, B.-J.; Shi, Z.-J. Tetrahedron 2012, 68, 5130-5136
11. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068-5083
12. Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem. Eur. J. 2010, 16, 2654-2672
13. Chen, D. Y.-K.; Youn, S. W. Chem. Eur. J. 2012, 18, 9452-9474
14. Li, C.-J. Acc. Chem. Res. 2009, 42, 335-344
15. Le Bras, J.; Muzart, J. Chem. Rev. 2011, 111, 1170-1214
16. Ferreira, E. M.; Zhang, H.; Stoltz, B. M. In The Mizoroki-Heck Reaction; Oestreich, M., Ed.; Wiley: New York, 2009; Chapter 9, pp 345-382.
17. Karimi, B.; Behzadnia, H.; Elhamifar, D.; Akhavari, P. F.; Eshafani, F. K.; Zamani, A. Synthesis 2010, 1399-1427
18. Muzart, J. Chem. Asian J. 2006, 1, 508-515
19. Piera, J.; Bäckvall, J.-E. Angew. Chem., Int. Ed. 2008, 47, 3506-3523
20. Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420
21. Stahl, S. S. Science 2005, 309, 1824-1826
22. Shi, Z.; Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3381-3430
23. Gligorich, K. M.; Sigman, M. S. Angew. Chem., Int. Ed. 2006, 45, 6612-6615
24. Min, M.; Kim, Y.; Hong, S. Chem. Commun. 2013, 49, 196-198
25. Obora, Y.; Ishi, Y. Molecules 2010, 15, 1487-1500
26. Zhang, Y.-H.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 5072-5074
27. Dams, M.; De Vos, D. E.; Celen, S.; Jacobs, P. A. Angew. Chem., Int. Ed. 2003, 42, 3512-3515
28. Harakat, D.; Muzart, J.; Le Bras, J. Adv. Synth. Catal. 2013, 355, 59-67
29. Liu, X.; Hii, K. K. Mimi J. Org. Chem. 2011, 76, 8022-8026
30. Nishikata, T.; Lipshutz, B. H. Org. Lett. 2010, 12, 1972-1975
31. Beck, E. M.; Grimster, N. P.; Hatley, R.; Gaunt, M. J. J. Am. Chem. Soc. 2006, 128, 2528-2529
32. Wenzel-Delord, J.; Dröge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740-4761
33. PlazÌuk, D.; Zakrzewski, J.; Salmain, M. Org. Biomol. Chem. 2011, 9, 408-417
34. Piotrowicz, M.; Zakrzewski, J.; Makal, A.; BaÌ̈k, J.; Malińska, M.; Woźniak, K. J. Organomet. Chem. 2011, 696, 3499-3506
35. Pearson, A. J. Metallo-organic Chemistry; Wiley: Chichester, U.K., 1985; p 313.
36. ŠteÌpnička, P., Ed. Ferrocenes: Ligands, Materials and Biomolecules; Wiley: Chichester, U.K., 2008.
37. Togni, A.; Hayashi, T., Eds. Ferrocenes: Homogenous Catalysis, Organic Synthesis, Materials Science; VCH: Weinheim, Germany, 1995.
38. Jaouen, G., Ed. Bioorganometallics; Wiley-VCH: Weinheim, Germany, 2006.
39. van Staveren, D. R.; Metzler-Nolte, N. Chem. Rev. 2004, 104, 5931-5985
40. Fouda, M. F. R.; Abd-Elzaher, M. M.; Abdelsamaia, R. A.; Labib, A. A. Appl. Organomet. Chem. 2007, 21, 613-625
41. Seiwert, B.; Karst, U. Anal. Bioanal. Chem. 2008, 390, 181-200
42. Neuse, E. W. J. Inorg. Organomet. Polym. Mater. 2005, 15, 3-32
43. Kraatz, H.-B. J. Inorg. Organomet. Polym. Mater. 2005, 15, 83-106
44. Zatsepin, T. S.; Andreev, Yu. S.; Hianik, T.; Oretskaya, T. S. Russ. Chem. Rev. 2003, 72, 537-554
45. Fujiwara, Y.; Asano, R.; Moritani, I. J. Org. Chem. 1976, 41, 1680-1683
46. Asano, R.; Moritani, I.; Sonoda, A. J. Chem. Soc. C 1971, 3691-3692
47. Asano, R.; Moritani, I.; Fujiwara, Y. J. Chem. Soc., Chem. Commun. 1970, 1293
48. Singh, K. S.; Dixneuf, P. H. Organometallics 2012, 31, 7320-7323
49. Fomin, V. M.; Markin, A. V. J. Therm. Anal. Calorim. 2008, 92, 985-987
50. Campbell, A. N.; Stahl, S. S. Acc. Chem. Res. 2012, 45, 851-863
51. Campbell, A. N.; White, P. B.; Guzel, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2010, 132, 15116-15119
52. Diao, T.; Wadzinski, T. J.; Stahl, S. S. Chem. Sci. 2012, 3, 887-891
53. Gao, W.; He, Z.; Qian, Y.; Huang, Y. Chem. Sci. 2012, 3, 883-886
54. Aguila, D.; Escribano, E.; Speed, S.; Talancon, D.; Yerman, L.; Alvarez, S. Dalton Trans. 2009, 6610-6625
55. Kubota, A.; Emmert, M. H.; Sanford, M. S. Org. Lett. 2012, 14, 1760-1763
56. Wang, D.-H.; Engle, K. M.; Shi, B.-F.; Yu, J.-Q. Science 2010, 327, 315-319
57. Zhang, Y.-H.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 5072-5074
58. Kandukuri, S. R.; Schiffner, J. A.; Oestreich, M. Angew. Chem., Int. Ed. 2011, 50, 1-6
59. Zhang, S.; Shi, L.; Ding, Y. J. Am. Chem. Soc. 2011, 133, 20218-20229
60. Evchenko, S. V.; Kamounah, F. S.; Schaumburg, K. J. Labelled Compd. Radiopharm. 2005, 48, 209-218
61. Simmons, E. M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 3066-3072
62. Jones, W. D. Acc. Chem. Res. 2003, 36, 140-146
63. Takebayashi, S.; Shizuno, T.; Otani, T.; Shibata, T. Beilstein J. Org. Chem. 2012, 8, 1844-1848
64. Xia, J.-B.; You, S.-L. Organometallics 2007, 26, 4869-4871
65. Zhang, H.; Cui, X.; Yao, X.; Wang, H.; Zhang, J.; Wu, Y. Org. Lett. 2012, 14, 3012-3015
66. Liu, W.; Cao, H.; Lei, A. Angew. Chem., Int. Ed. 2010, 49, 1-6
67. Datta, A.; Köllhofer, A.; Plenio, H. Chem. Commun. 2004, 1508-1509