Catalytic activation of diazo compounds using electron-rich, defined iron complexes for carbene-transfer reactions

Angewandte Chemie - International Edition

Volumn 51, Issue 22, 2012, Pages 5351-5354

  Holzwarth, Michael S ^a   Alt, Isabel ^a   Plietker, Bernd ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

carbenes; homogeneous catalysis; iron; rearrangements; thioethers

Indexed keywords

CARBENE TRANSFER; CARBENES; CATALYTIC ACTIVATION; DIAZO COMPOUNDS; DIAZO REAGENTS; ELECTRON-RICH; HIGH STABILITY; HOMOGENEOUS CATALYSIS; IN-SITU; IRON COMPLEX; REARRANGEMENTS; THIOETHERS;

CATALYSIS; IRON; ORGANIC COMPOUNDS; REACTION KINETICS;

IRON COMPOUNDS;

EID: 84861494654     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201201409     Document Type: Article

References (60)

1. R. G. Salomon, J. K. Kochi, J. Am. Chem. Soc. 1973, 95, 3300.
2. S. J. Mahmood, A. K. Saha, M. M. Hossain, Tetrahedron 1998, 54, 349.
3. V. K. Aggarwal, H. Abdel-Rahman, R. V. H. Jones, H. Y. Lee, B. D. Reid, J. Am. Chem. Soc. 1994, 116, 5973.
4. V. K. Aggarwal, J. R. Fulton, C. G. Sheldon, J. deVicente, J. Am. Chem. Soc. 2003, 125, 6034.
5. F. F. West, in Nitrogen, Oxygen and Sulfur Ylide Chemistry: A Practical Approach in Chemistry (Ed.:, J.S. Clark,), Oxford University, Oxford, 2002, p. 115
6. A. Saba, Tetrahedron Lett. 2003, 44, 2895
7. F. F. West, in Modern Rhodium-Catalyzed Organic Reactions (Ed.:, P.A. Evans,), Wiley-VCH, Weinheim, 2005, p. 417
8. J. Sweeney, Chem. Soc. Rev. 2009, 38, 1027
9. A. Sharma, L. Guénée, J.-V. Naubron, J. Lacour, Angew. Chem. 2011, 123, 3761
10. Angew. Chem. Int. Ed. 2011, 50, 3677.
11. M. P. Doyle, Chem. Rev. 1986, 86, 919
12. M. P. Doyle, R. Duffy, M. Ratnikov, L. Zhou, Chem. Rev. 2010, 110, 704
13. M. P. Doyle, D. C. Forbes, Chem. Rev. 1998, 98, 911
14. M. MarDíaz-Requejo, P. J. Pérez, Chem. Rev. 2008, 108, 3379.
15. See Ref.[1]
16. D. L. Christenson, C. J. Tokar, W. B. Tolman, Organometallics 1995, 14, 2148.
17. G. Maas, Chem. Soc. Rev. 2004, 33, 183.
18. S. E. Denmark, R. A. Stavenger, A.-M. Faucher, J. P. Edwards, J. Org. Chem. 1997, 62, 3375
19. C. Peng, J. Cheng, J. Wang, J. Am. Chem. Soc. 2007, 129, 8708.
20. A. Nakamura, A. Konishi, R. Tsujitani, M.-a. Kudo, S. Otsuka, J. Am. Chem. Soc. 1978, 100, 3449
21. Y. Chen, J. V. Ruppel, X. P. Zhang, J. Am. Chem. Soc. 2007, 129, 12074
22. K. B. Fields, J. T. Engle, S. Sripothongnak, C. Kim, X. P. Zhang, C. J. Ziegler, Chem. Commun. 2011, 47, 749.
23. W. J. Seitz, A. K. Saha, M. M. Hossain, Organometallics 1993, 12, 2604
24. J. R. Wolf, C. G. Hamaker, J.-P. Djukic, T. Kodadek, L. K. Woo, J. Am. Chem. Soc. 1995, 117, 9194
25. S. K. Edulji, S. T. Nguyen, Organometallics 2003, 22, 3374
26. T.-S. Lai, F.-Y. Chan, P.-K. So, D.-L. Ma, K.-Y. Wong, C.-M. Che, Dalton Trans. 2006, 4845.
27. P. W. Davies, S. J.-C. Albrecht, G. Assanelli, Org. Biomol. Chem. 2009, 7, 1276
28. A. Caballero, E. Despagnet-Ayoub, M. M. Díaz-Requejo, A. Díaz-Rodríguez, M. E. González-Núñez, R. Mello, B. K. Muñoz, W.-S. Ojo, G. Asensio, M. Etienne, P. J. Pérez, Science 2011, 332, 835.
29. For a monography on carbene intermediates see: Carbene Chemistry: From Fleeting Intermediate to Powerful Reagents (Ed.:, G. Bertrand,), Marcel Dekker, New York, 2002.
30. B. Plietker, Angew. Chem. 2006, 118, 1497
31. Angew. Chem. Int. Ed. 2006, 45, 1469
32. B. Plietker, Angew. Chem. 2006, 118, 6200
33. Angew. Chem. Int. Ed. 2006, 45, 6053
34. B. Plietker, A. Dieskau, K. Möws, A. Jatsch, Angew. Chem. 2008, 119, 202
35. Angew. Chem. Int. Ed. 2008, 47, 198
36. M. Holzwarth, A. Dieskau, M. Tabassam, B. Plietker, Angew. Chem. 2009, 121, 7387
37. Angew. Chem. Int. Ed. 2009, 48, 7251
38. M. Jegelka, B. Plietker, Chem. Eur. J. 2011, 17, 10417
39. M. S. Holzwarth, W. Frey, B. Plietker, Chem. Commun. 2011, 47, 11113
40. A. P. Dieskau, B. Plietker, Org. Lett. 2011, 13, 5544
41. S. Magens, B. Plietker, Chem. Eur. J. 2011, 17, 8807
42. A. P. Dieskau, J.-M. Begouin, B. Plietker, Eur. J. Org. Chem. 2011, 5291
43. A. P. Dieskau, M. S. Holzwarth, B. Plietker, Chem. Eur. J. 2012, 18, 2423.
44. Modern Carbonyl Olefination: Methods and Applications (Ed.:, T. Takeda,), Wiley-VCH, Weinheim, 2006.
45. Metal Carbenes in Organic Synthesis (Ed.:, F. ZaragozaDörwald,), Wiley-VCH, Weinheim, 1999.
46. W. Kirmse, M. Kapps, Chem. Ber. 1968, 101, 994
47. M. P. Doyle, W. H. Tamblyn, V. Bagheri, J. Org. Chem. 1981, 46, 5094
48. D. S. Carter, D. L. VanVranken, Org. Lett. 2000, 2, 1303
49. R. Prabharasuth, D. L. VanVranken, J. Org. Chem. 2001, 66, 5256.
50. While these studies were underway an efficient iron-catalyzed Wittig olefination was reported:, P. Wang, C.-R. Liu, X.-L. Sun, S.-S. Chen, J.-F. Li, Z. Xie, Y. Tang, Chem. Commun. 2012, 48, 290.
51. B. Morandi, B. Mariampillai, E. M. Carreira, Angew. Chem. 2011, 123, 1133
52. Angew. Chem. Int. Ed. 2011, 50, 1101
53. B. Morandi, E. M. Carreira, Org. Lett. 2011, 13, 5984
54. B. Morandi, E. M. Carreira, Angew. Chem. 2010, 122, 950
55. Angew. Chem. Int. Ed. 2010, 49, 938
56. B. Morandi, J. Cheang, E. M. Carreira, Org. Lett. 2011, 13, 3080
57. B. Morandi, E. M. Carreira, Angew. Chem. 2010, 122, 4390
58. Angew. Chem. Int. Ed. 2010, 49, 4294
59. B. Morandi, E. M. Carreira, Angew. Chem. 2011, 123, 9251
60. Angew. Chem. Int. Ed. 2011, 50, 9085.