A synthetic and mechanistic investigation of the chromium tricarbonyl-mediated Masamune-Bergman cyclization. direct observation of a ground-state triplet p-benzyne biradical

Organometallics

Volumn 31, Issue 15, 2012, Pages 5396-5404

  Ylijoki, Kai E O ^a   Lavy, Séverine ^a   Fretzen, Angelika ^a,b   Kündig, E Peter ^a   Berclaz, Théo ^a   Bernardinelli, Gérald ^a   Besnard, Céline ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

^b IRONWOOD PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE COORDINATION; BOND FORMATION; COORDINATING SOLVENTS; CYCLOAROMATIZATION; DIASTEREOCONTROL; ENEDIYNES; EPR SPECTROSCOPY; HYDROGEN ATOMS; INTERSYSTEM CROSSING; ROOM TEMPERATURE; SPECTROSCOPIC METHOD; TRIPLET STATE;

CHROMIUM; CHROMIUM COMPOUNDS; GROUND STATE; HYDROGEN; NAPHTHALENE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; ORGANIC COMPOUNDS; SPECTROSCOPIC ANALYSIS;

CYCLIZATION;

EID: 84865012875     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om300427j     Document Type: Article

References (67)

1. Darby, N.; Kim, C. U.; Salaün, J. A.; Shelton, K. W.; Takada, S.; Masamune, S. Chem. Commun. 1971, 1516
2. Jones, R. B.; Bergman, R. G. J. Am. Chem. Soc. 1972, 94, 660
3. Johnson, G. C.; Stofko, J. J., Jr.; Lockhart, T. P.; Brown, D. W.; Bergman, R. G. J. Org. Chem. 1979, 44, 4215
4. Lockhart, T. P.; Mallon, C. B.; Bergman, R. G. J. Am. Chem. Soc. 1980, 102, 5976
5. Lockhart, T. P.; Comita, P. B.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4082
6. Lockhart, T. P.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4091
7. Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502
8. Galm, U.; Hager, M. H.; Van Lanen, S. G.; Ju, J.; Thorson, J. S.; Shen, B. Chem. Rev. 2005, 105, 739
9. Joshi, M. C.; Rawat, D. S. Chem. Biodiversity 2012, 9, 459
10. Fretzen, A.; Ripa, A.; Liu, R. G.; Bernardinelli, G.; Kündig, E. P. Chem.-Eur. J. 1998, 4, 251
11. Fretzen, A.; Kündig, E. P. Helv. Chim. Acta 1997, 80, 2023
12. Pape, A. R.; Kaliappan, K. P.; Kündig, E. P. Chem. Rev. 2000, 100, 2917
13. Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc. 1993, 115, 4419
14. Shair, M. D.; Yoon, T.-Y.; Mosny, K. K.; Chou, T. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 9509
15. Nicolaou, K. C.; Zuccarello, G.; Riemer, C.; Estevez, V. A.; Dai, W.-M. J. Am. Chem. Soc. 1992, 114, 7360
16. O'Connor, J. M.; Lee, L. I.; Gantzel, P.; Rheingold, A. L.; Lam, K.-C. J. Am. Chem. Soc. 2000, 122, 12057
17. O'Connor, J. M.; Friese, S. J.; Tichenor, M. J. Am. Chem. Soc. 2002, 124, 3506
18. O'Connor, J. M.; Friese, S. J.; Rodgers, B. L. J. Am. Chem. Soc. 2005, 127, 16342
19. O'Connor, J. M.; Friese, S. J. Organometallics 2008, 27, 4280
20. Enriquez-Garcia, A.; Ouizem, S.; Cheng, X.; Romanens, P.; Kündig, E. P. Adv. Synth. Catal. 2010, 352, 2306
21. Mercier, A.; Urbaneja, X.; Yeo, W. C.; Chaudhuri, P. D.; Cumming, G. R.; House, D.; Bernardinelli, G.; Kündig, E. P. Chem.-Eur. J. 2010, 16, 6285
22. Lavy, S.; Pérez-Luna, A.; Kündig, E. P. Synlett 2008, 2621
23. Cumming, G. R.; Bernardinelli, G.; Kündig, E. P. Chem.-Asian J. 2006, 1, 459
24. Kündig, E. P.; Perret, C.; Spichiger, S.; Bernardinelli, G. J. Organomet. Chem. 1985, 286, 183
25. Zhang, S.; Shen, J. K.; Basolo, F.; Ju, T. D.; Lang, R. F.; Kiss, G.; Hoff, C. D. Organometallics 1994, 13, 3692
26. Kündig, E. P.; Pape, A. Top. Organomet. Chem. 2004, 7, 71
27. Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207
28. Teobald, B. J. Tetrahedron 2002, 58, 4133
29. Magnus, P.; Carter, P. A. J. Am. Chem. Soc. 1988, 110, 1626
30. Magnus, P.; Lewis, R. T.; Huffman, J. C. J. Am. Chem. Soc. 1988, 110, 6921
31. 2 = 0.048, and S = 1.76. Computing details: Data collection, cell refinement, and data reduction, STOE X-AREA; structure solution, Superflip; structure refinement, CRYSTALS. CCDC-882300 contains the supplementary crystallographic data for 16. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.; Fax: (+44) 1223-336-033; or E-mail: deposit@ccdc.cam.ac.uk).
32. Kündig, E. P. Top. Organomet. Chem. 2004, 7, 3
33. O'Connor, J. M. Personal communication. Geneva, 2011.
34. UB3LYP gives reliable energetics for thermal Bergman cyclizations: Gräfenstein, J.; Hjerpe, A. M.; Kraka, E.; Cremer, D. J. Phys. Chem. A 2000, 104, 1748
35. McMahon, R. J.; Halter, R. J.; Fimmen, R. L.; Wilson, R. J.; Peebles, S. A.; Kuczkowski, R. L.; Stanton, J. F. J. Am. Chem. Soc. 2000, 122, 939
36. Usuki, T.; Inoue, M.; Akiyama, K.; Hirama, M. Chem. Lett. 2002, 31, 1148
37. Usuki, T.; Mita, T.; Lear, M. J.; Das, P.; Yoshimura, F.; Inoue, M.; Hirama, M.; Akiyama, K.; Tero-Kubota, S. Angew. Chem., Int. Ed. 2004, 43, 5249
38. Usuki, T.; Inoue, M.; Akiyama, K.; Hirama, M. Biorg. Med. Chem. 2005, 13, 5218
39. Usuki, T.; Nakanishi, K.; Ellestad, G. A. Org. Lett. 2006, 8, 5461
40. Usuki, T.; Kawai, M.; Nakanishi, K.; Ellestad, G. A. Chem. Commun. 2010, 46, 737
41. Kraka, E.; Cremer, D. J. Am. Chem. Soc. 1994, 116, 4929
42. Cramer, C. J.; Nash, J. J.; Squires, R. R. Chem. Phys. Lett. 1997, 277, 311
43. Cramer, C. J.; Debbert, S. Chem. Phys. Lett. 1998, 287, 320
44. Chen, W.-C.; Chang, N.-Y.; Yu, C.-H. J. Phys. Chem. A 1998, 102, 2484
45. Jones, G. B.; Warner, P. M. J. Am. Chem. Soc. 2001, 123, 2134
46. Clark, A. E.; Davidson, E. R. J. Org. Chem. 2003, 68, 3387
47. Wang, E. B.; Parish, C. A.; Lishka, H. J. Chem. Phys. 2008, 129, 44306
48. Li, X.; Paidus, J. J. Chem. Phys. 2008, 129, 174101
49. Karton, A.; Kaminker, I.; Martin, J. M. L. J. Phys. Chem. A 2009, 113, 7610
50. Wenthold, P. G.; Squires, R. R.; Lineberger, W. C. J. Am. Chem. Soc. 1998, 120, 5279
51. Logan, C. F.; Chen, P. J. Am. Chem. Soc. 1996, 118, 2113
52. Schottelius, M. J.; Chen, P. J. Am. Chem. Soc. 1996, 118, 4896
53. Kaptein, R. Adv. Free-Radical Chem. 1975, 5, 338
54. Spartan '10; Wavefunction, Inc.; Irvine, CA, 2011; http://www.wavefun. com.
55. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209
56. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221
57. Stewart, J. J. P. J. Comput. Chem. 1991, 12, 320
58. Stewart, J. J. P. J. Mol. Model. 2004, 10, 155
59. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
60. Becke, A. D. J. Chem. Phys. 1993, 98, 1372
61. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
62. Crowther, G. P.; Sundberg, R. J.; Sarpeshkar, A. M. J. Org. Chem. 1984, 49, 4657
63. Kündig, E. P.; Sau, M.; Perez-Luna, A. Synlett 2006, 2114
64. Basak, A.; Shain, J. C.; Khamrai, U. K.; Rudra, K. R. J. Chem. Soc., Perkin Trans. 1 2000, 1955
65. Faller, J. W.; Crabtree, R. H.; Habib, A. Organometallics 1985, 4, 929
66. Steinmetz, S.; Schenk, W. A. Organometallics 1999, 18, 943
67. Desobry, V.; Kündig, E. P. Helv. Chim. Acta 1981, 64, 1288