Chromium-catalyzed radical cyclization of bromo and chloro acetals

Organometallics

Volumn 29, Issue 24, 2010, Pages 6639-6641

  MacLeod, K Cory ^a   Patrick, Brian O ^b   Smith, Kevin M ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CR COMPLEXES; CYCLIZED PRODUCTS; CYCLOPENTADIENYLS; DIKETIMINATES; HYDROGEN ATOMS; RADICAL CYCLIZATIONS; REDUCTANTS; TERPINENE;

CHROMIUM; CHROMIUM COMPOUNDS; MANGANESE; PHOTOLYSIS;

CYCLIZATION;

EID: 78650655019     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om101068r     Document Type: Article

References (61)

1. Rudolph, A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 2656-2670
2. Poli, R. Angew. Chem., Int. Ed. 2006, 45, 5058-5070
3. Ouchi, M.; Terashima, T.; Sawamoto, M. Chem. Rev. 2009, 109, 4963-5050
4. Smith, K. M.; McNeil, W. S.; Abd-El-Aziz, A. S. Macromol. Chem. Phys. 2010, 211, 10-16
5. di Lena, F.; Matyjaszewski, K. Prog. Polym. Sci. 2010, 35, 959-1021
6. Champouret, Y.; MacLeod, K. C.; Baisch, U.; Patrick, B. O.; Smith, K. M.; Poli, R. Organometallics 2010, 29, 167-176
7. MacLeod, K. C.; Conway, J. L.; Patrick, B. O.; Smith, K. M. J. Am. Chem. Soc. ASAP (DOI: 10.1021/ja1083392).
8. Schrauzer, G. N. Acc. Chem. Res. 1968, 1, 97-103
9. Halpern, J. Acc. Chem. Res. 1982, 15, 238-244
10. Samsel, E. G.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 4790-4804
11. Daikh, B. E.; Finke, R. G. J. Am. Chem. Soc. 1992, 114, 2938-2943
12. Gridnev, A. A.; Ittel, S. D. Chem. Rev. 2001, 101, 3611-3659
13. Debuigne, A.; Poli, R.; Jérome, C.; Jérome, R.; Detrembleur, C. Prog. Polym. Sci. 2009, 34, 211-239
14. Sherwood, R. K.; Kent, C. L.; Patrick, B. O.; McNeil, W. S. Chem. Commun. 2010, 46, 2456-2458
15. Hu, X.; Brunschwig, B. S.; Peters, J. C. J. Am. Chem. Soc. 2007, 129, 8988-8998
16. Dempsey, J. L.; Brunschwig, B. S.; Winkler, J. R.; Gray, H. B. Acc. Chem. Res. 2009, 42, 1995-2004
17. Okabe, M.; Tada, M. J. Org. Chem. 1982, 47, 5382-5384
18. Giese, B.; Erdmann, P.; Göbel, T.; Springer, R. Tetrahedron Lett. 1992, 33, 4545-4548
19. Braunchaud, B. P.; Yu, G.-X. Organometallics 1993, 12, 4262-4264
20. Johnson, M. D. Acc. Chem. Res. 1983, 16, 343-349
21. Pattenden, G. Chem. Soc. Rev. 1988, 17, 361-382
22. Iqbal, J.; Bhatla, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519-564
23. Cahiez, G.; Moyeux, A. Chem. Rev. 2010, 110, 1435-1462
24. Fryzuk, M. D.; Leznoff, D. B.; Thompson, R. C.; Rettig, S. J. J. Am. Chem. Soc. 1998, 120, 10126-10135
25. Langlotz, B. K.; Fillol, J. L.; Gross, J. H.; Wadepohl, H.; Gade, L. H. Chem.-Eur. J. 2008, 14, 10267-10279
26. Dutta, G.; Kumar, K.; Gupta, B. D. Organometallics 2009, 28, 3485-3491
27. Vincent, J. Dalton Trans. 2010, 39, 3787-3794
28. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564-5566
29. Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741-3742
30. Salom-Roig, X. J.; Dénes, F.; Renaud, P. Synthesis 2004, 1903-1928
31. Vaupel, A.; Knochel, P. J. Org. Chem. 1996, 61, 5743-5753
32. Phapale, V. B.; Buñuel, E.; García-Iglesias, M.; Cárdenas, D. J. Angew. Chem., Int. Ed. 2007, 46, 8790-8795
33. Wakabayashi, K.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 5374-5375
34. Ohmiya, H.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2006, 128, 1886-1889
35. Affo, W.; Ohmiya, H.; Fujioka, T.; Ikeda, Y.; Nakamura, T.; Yorimitsu, H.; Oshima, K.; Imamura, Y.; Mizuta, T.; Miyoshi, K. J. Am. Chem. Soc. 2006, 128, 8068-8077
36. Someya, H.; Kondoh, A.; Sato, A.; Ohmiya, H.; Yorimitsu, H.; Oshima, K. Synlett 2006, 3061-3064
37. Zhou, L.; Hirao, T. J. Org. Chem. 2003, 68, 1633-1635
38. Fürstner, A.; Martin, R.; Krause, H.; Seidel, G.; Goddard, R.; Lehmann, C. W. J. Am. Chem. Soc. 2008, 130, 8773-8787
39. Fujita, K.; Nakamura, T.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 3137-3138
40. Fujita, K.; Yorimitsu, H.; Oshima, K. Synlett 2002, 337-339
41. Fujita, K.; Yorimitsu, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2004, 77, 1727-1736
42. Fujita, K.; Yorimitsu, H.; Oshima, K. Chem. Rec. 2004, 4, 110-119
43. Fürstner, A. Chem. Rev. 1999, 99, 991-1045
44. Smith, K. M. Coord. Chem. Rev. 2006, 250, 1023-1031
45. Espenson, J. H. Prog. Inorg. Chem. 1983, 30, 189-212
46. Wessjohann, L. A.; Schmidt, G.; Schrekker, H. S. Tetrahedron 2008, 64, 2134-2142
47. Luinstra, G. A.; Teuben, J. H. J. Chem. Soc., Chem. Commun. 1990, 1470-1471
48. Doherty, J. C.; Ballem, K. H. D.; Patrick, B. O.; Smith, K. M. Organometallics 2004, 23, 1487-1489
49. Gansäuer, A.; Fleckhaus, A.; Lafont, M. A.; Okkel, A.; Kotsis, K.; Anoop, A.; Neese, F. J. Am. Chem. Soc. 2009, 131, 16989-16999
50. Gansäuer, A.; Shi, L.; Otte, M. J. Am. Chem. Soc. 2010, 132, 11858-11859
51. Warren, J. J.; Tronic, T. A.; Mayer, J. M. Chem. Rev. ASAP (doi: 10.1021/cr100085k).
52. 2 to activate managanese metal, see: Takai, K.; Ueda, T.; Hayashi, T.; Moriwake, T. Tetrahedron Lett. 1996, 37, 7049-7052
53. Barczak, N. T.; Jarvo, E. R. Eur. J. Org. Chem. 2008, 5507-5510
54. Layfield, R. A. Chem. Soc. Rev. 2008, 37, 1098-1107
55. Cahiez, G.; Duplais, C.; Buendia, J. Chem. Rev. 2009, 109, 1434-1476
56. Everson, D. A.; Shrestha, R.; Weix, D. J. J. Am. Chem. Soc. 2010, 132, 920-921
57. Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461-1473
58. Fu, G. C. Acc. Chem. Res. 2008, 41, 1555-1564
59. Kliegman, S.; McNeill, K. Dalton Trans. 2008, 4191-4201
60. Zhu, D.; Budzelaar, P. H. M. Organometallics 2010, 29, 5759 - 5761.
61. For the radical cyclization of the prenyl ether of 2-chlorophenol with a cobalt catalyst, see ref 14e.