Metalloradical approach to 2H -chromenes

Journal of the American Chemical Society

Volumn 136, Issue 3, 2014, Pages 1090-1096

  Paul, Nanda D ^a   Mandal, Sutanuva ^a   Otte, Matthias ^a   Cui, Xin ^b   Zhang, X Peter ^b   De Bruin, Bas ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT COMPLEXES; EPR SPECTROSCOPY; HYDROGEN ATOM TRANSFERS (HAT); N-TOSYLHYDRAZONES; RADICAL ADDITION; RADICAL MECHANISM; RING-CLOSING REACTIONS; SUBSTITUTION PATTERNS;

ATOMS; COBALT; REACTION INTERMEDIATES;

FREE RADICAL REACTIONS;

2H 1 BENZOPYRAN DERIVATIVE; ALKYNE; CARBENE; CHROMENE DERIVATIVE; COBALT DERIVATIVE; HYDRAZONE DERIVATIVE; HYDROGEN; HYDROXYL GROUP; PORPHYRIN DERIVATIVE; RADICAL; SALICYLIC ACID; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; DRUG STRUCTURE; ELECTRON SPIN RESONANCE; METALLORADICAL REACTION; RING CLOSING METATHESIS;

BENZOPYRANS; CATALYSIS; COBALT; FREE RADICALS; METHANE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 84893015593     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4111336     Document Type: Article

References (73)

1. Covington, A. D. Chem. Soc. Rev. 1997, 111
2. Ellis, G. P., Ed. Chromenes, Chromanones, and Chromones. In The Chemistry of Heterocyclic Compounds; Wiley-Interscience: New York, 1977; Vol. 31.
3. Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds. Comprehensive Heterocyclic Chemistry II; Pergamon: Oxford, 1996; Vol. 2.
4. Schneider, P.; Hawser, S.; Islam, K. Bioorg. Med. Chem. Lett. 2003, 13, 4217
5. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 9074
6. Elomri, A.; Mitaku, S.; Michel, S.; Skaltsounis, A.-L.; Tillequin, F.; Koch, M.; Pierre, A.; Guilbaud, N.; Leonce, S.; Kraus-Berthier, L.; Rolland, Y.; Atassi, G. J. Med. Chem. 1996, 39, 4762
7. Jankun, J.; Selman, S. H.; Swiercz, R.; Skrzypczak-Jankun, E. Nature 1997, 387, 56
8. Mukai, K.; Okabe, K.; Hosose, H. J. Org. Chem. 1989, 54, 557
9. Lago, J. H. G.; Ramos, C. S.; Casanova, D. C. C.; Morandim, A. D.; Bergamo, D. C. B.; Cavalheiro, A. J.; Bolzani, V. D.; Furlan, M.; Guimaraes, E. F.; Young, M. C. M.; Kato, M. J. J. Nat. Prod. 2004, 67, 1783
10. Gauthier, S.; Caron, B.; Cloutier, J.; Dory, Y. L.; Favre, A.; Larouche, D.; Mailhot, J.; Ouellet, C.; Schwerdtfeger, A.; Leblanc, G.; Martel, C.; Simard, J.; Merand, Y.; Belanger, A.; Labrie, C.; Labrie, F. J. Med. Chem. 1997, 40, 2117
11. Bauer, D. J.; Selway, J. W. T.; Batchelor, J. F.; Tisdale, M.; Caldwell, I. C.; Young, D. A. B. Nature 1981, 292, 369
12. Terregroza, I.; Evans, T.; Das, B. C. Chem. Biol. Drug. Des. 2009, 73, 339
13. Xu, G.; Yang, G.; Wang, C.; Fan, S.; Xie, L.; Gao, Y. Molecules 2013, 18, 11964
14. Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q. Angew. Chem., Int. Ed. 2000, 39, 734
15. Nicolaou, K. C.; Cao, G.-Q.; Pfefferkorn, J. A. Angew. Chem., Int. Ed. 2000, 39, 739
16. Thomas, N.; Zachariah, S. N. Asian J. Pharm. Clin. Res. 2013, 6/2, 11
17. Bamfield, P.; Hutchings, M. G. Chromic Phenomena: The Technological Applications of Colour Chemistry; The Royal Society of Chemistry: Cambridge, UK, 2010.
18. Pina, F.; Melo, M. J.; Laia, C. A. T.; Parola, J.; Lima, J. C. Chem. Soc. Rev. 2012, 41, 869
19. Majumdar, N.; Korthals, K. A.; Wulff, W. D. J. Am. Chem. Soc. 2012, 134, 1357
20. Graham, T. J. A.; Doyle, A. G. Org. Lett. 2012, 14, 1616
21. Iyer, M.; Trivedi, G. R. Synth. Commun. 1990, 20, 1347
22. Hlubeck, J.; Ritchie, E.; Taylor, W. C. Tetrahedron Lett. 1969, 1369
23. Chang, S.; Grubbs, R. H. J. Org. Chem. 1998, 63, 864
24. Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343
25. Brimble, M.; Jay-Smith, M.; Furkert, D.; Sperry, J. Synlett 2011, 1395
26. Doodeman, R.; Rutjes, F. P. J. T.; Hiemstra, H. Tetrahedron Lett. 2000, 41, 5979
27. Li, X.; Reuman, M.; Russell, R. K.; Adams, R.; Ma, R.; Branum, S.; Youells, S.; Roberts, J.; Jain, N.; Kanojia, R.; Sui, Z. Org. Process Res. Dev. 2007, 11, 414
28. Grese, T. A.; Pennington, L. D. Tetrahedron. Lett. 1995, 36, 8913
29. Walkinshaw, A. J.; Xu, W.; Suero, M. G.; Gaunt, M. J. J. Am. Chem. Soc. 2013, 135, 12532
30. Wang, Q.; Finn, M. G. Org. Lett. 2000, 2, 4063
31. Liu, F.; Evans, T.; Das, B. C. Tetrahedron Let. 2008, 49, 1578
32. Moquist, P. N.; Kodama, T.; Schaus, S. E. Angew. Chem., Int. Ed. 2010, 49, 7096
33. Doyle, M. P. Angew. Chem. 2009, 121, 864
34. Angew. Chem., Int. Ed. 2009, 48, 850.
35. Huang, L. Y.; Chen, Y.; Gao, G. Y.; Zhang, X. P. J. Org. Chem. 2003, 68, 8179
36. Penoni, A.; Wanke, R.; Tollari, S.; Gallo, E.; Musella, D.; Ragaini, F.; Demartin, F.; Cenini, S. Eur. J. Inorg. Chem. 2003, 1452
37. Chen, Y.; Zhang, X. P. J. Org. Chem. 2007, 72, 5931
38. Chen, Y.; Ruppel, J. V.; Zhang, X. P. J. Am. Chem. Soc. 2007, 129, 12074
39. Zhu, S. F.; Ruppel, J. V.; Lu, H. J.; Wojtas, L.; Zhang, X. P. J. Am. Chem. Soc. 2008, 130, 5042
40. Zhu, S. F.; Perman, J. A.; Zhang, X. P. Angew. Chem., Int. Ed. 2008, 47, 8460
41. Fantauzzi, S.; Gallo, E.; Rose, E.; Raoul, N.; Caselli, A.; Issa, S.; Ragaini, F.; Cenini, S. Organometallics 2008, 27, 6143
42. Ruppel, J. V.; Gauthier, T. J.; Snyder, N. L.; Perman, J. A.; Zhang, X. P. Org. Lett. 2009, 11, 2273
43. Zhu, S. F.; Xu, X.; Perman, J. A.; Zhang, X. P. J. Am. Chem. Soc. 2010, 132, 12796
44. Chen, Y.; Zhang, X. P. J. Org. Chem. 2004, 69, 2431
45. Xu, X.; Zhu, S.; Cui, X.; Wojtas, L.; Zhang, X. P. Angew. Chem., Int. Ed. 2013, 52, 11857
46. Dzik, W. I.; Xu, X.; Zhang, X. P.; Reek, J. N. H.; de Bruin, B. J. Am. Chem. Soc. 2010, 132, 10891
47. Lu, H.; Dzik, W. I.; Xu, X.; Wojtas, L.; de Bruin, B.; Zhang, X. P. J. Am. Chem. Soc. 2011, 133, 8518
48. Dzik, W. I.; Zhang, X. P.; de Bruin, B. Inorg. Chem. 2011, 50, 9896
49. Dzik, W. I.; Reek, J. N. H.; de Bruin, B. Chem.-Eur. J. 2008, 14, 7594
50. Lyaskovskyy, V.; de Bruin, B. ACS Catal. 2012, 2, 270
51. Cui, X.; Xu, X.; Lu, H.; Zhu, S.; Wojtas, L.; Zhang, X. P. J. Am. Chem. Soc. 2011, 133, 3304
52. Cui, X.; Xu, X.; Wojtas, L.; Kim, M. M.; Zhang, X. P. J. Am. Chem. Soc. 2012, 134, 19981
53. Paul, N. D.; Chirila, A.; Lu, H.; Zhang, X. P.; de Bruin, B. Chem.-Eur. J. 2013, 19, 12953
54. Fulton, J. R.; Aggarwal, V. K.; de Vicente, J. Eur. J. Org. Chem. 2005, 1479
55. Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236
56. Xia, Y.; Liu, Z.; Xiao, Q.; Qu, P.; Ge, R.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2012, 51, 5714
57. Ye, F.; Ma, X.; Xiao, Q.; Li, H.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2012, 134, 5742
58. Zhou, L.; Shi, Y.; Xiao, Q.; Liu, Y.; Ye, F.; Zhang, Y.; Wang, J. Org. Lett. 2011, 13, 968
59. Lyaskovskyy, V.; Olivos Suárez, A. I.; Lu, H.; Jiang, H.; Zhang, X. P.; de Bruin, B. J. Am. Chem. Soc. 2011, 133, 12264
60. Olivos Suarez, A. I.; Jiang, H.; Zhang, X. P.; de Bruin, B. Dalton Trans. 2011, 40, 5697
61. Olivos Suarez, A. I.; Lyaskovskyy, V.; Reek, J. N. H.; van der Vlugt, J. I.; de Bruin, B. Angew. Chem., Int. Ed. 2013, 52, 12510
62. Parker, K. A.; Mindt, T. L. Org. Lett. 2001, 3, 3875
63. Sheshenev, A. E.; Baird, M. S.; Croft, A. K.; Bolesov, I. G. Tetrahedron 2009, 65, 10036 and references therein
64. Xu, X.; Zavalij, P. Y.; Doyle, M. P. J. Am. Chem. Soc. 2013, 135, 12439
65. Ahlrichs, R. Turbomole Version 6.4; Theoretical Chemistry Group, University of Karlsruhe.
66. PQS, version 2.4, 2001, Parallel Quantum Solutions, Fayetteville, Arkansas (USA) (the Baker optimizer is available separately from PQS upon request): Baker, I. J. Comput. Chem. 1986, 7, 385.
67. (the Baker optimizer is available separately from PQS upon request): Baker, I. J. Comput. Chem. 1986, 7, 385.
68. Budzelaar, P. H. M. J. Comput. Chem. 2007, 28, 2226
69. Becke, A. D. Phys. Rev. A 1988, 38, 3098
70. Perdew, J. P. Phys. Rev. B 1986, 33, 8822
71. Sierka, M.; Hogekamp, A.; Ahlrichs, R. J. Chem. Phys. 2003, 118, 9136
72. Schaefer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571
73. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104