Design of leaving groups in radical C-C fragmentations: Through-bond 2c-3e interactions in self-terminating radical cascades

Chemistry - A European Journal

Volumn 20, Issue 28, 2014, Pages 8664-8669

  Mondal, Sayantan ^a   Gold, Brian ^a   Mohamed, Rana K ^a   Alabugin, Igor V ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

alkynes; cyclization; domino reactions; radical reactions; through bond interactions

Indexed keywords

AROMATIZATION; CYCLIZATION; REACTION KINETICS;

ALKYNES; AROMATICITIES; CARBON-CARBON BOND; DOMINO REACTIONS; LEAVING GROUPS; RADICAL REACTIONS; THROUGH-BOND INTERACTIONS; TRANSITION STATE;

DESIGN;

EID: 84903714300     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201402843     Document Type: Article

References (67)

1. E. T. Chernick, R. R. Tykwinski, J. Phys. Org. Chem. 2013, 26, 742.
2. I. V. Alabugin, B. Gold, J. Org. Chem. 2013, 78, 7777.
3. K. Gilmore, I. V. Alabugin, Chem. Rev. 2011, 111, 6513
4. I. V. Alabugin, K. Gilmore, M. Manoharan, J. Am. Chem. Soc. 2011, 133, 12608
5. I. V. Alabugin, K. Gilmore, Chem. Commun. 2013, 49, 11246.
6. L. T. Scott, Angew. Chem. Int. Ed. 2004, 43, 4994
7. M. B. Goldfinger, T. M. Swager, J. Am. Chem. Soc. 1994, 116, 7895
8. U. H. F. Bunz, Chem. Rev. 2000, 100, 1605. Selected examples from our work
9. I. V. Alabugin, K. Gilmore, S. Patil, M. Manoharan, S. V. Kovalenko, R. J. Clark, I. Ghiviriga, J. Am. Chem. Soc. 2008, 130, 11535
10. P. Byers, I. V. Alabugin, J. Am. Chem. Soc. 2012, 134, 9609
11. P. M. Byers, J. I. Rashid, R. K. Mohamed, I. V. Alabugin, Org. Lett. 2012, 14, 6032
12. K. Pati, A. M. Hughes, H. Phan, I. V. Alabugin, Chem. Eur. J. 2014, 20, 390.
13. S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders, J. F. Stoddart, Angew. Chem. 2002, 114, 938
14. Angew. Chem. Int. Ed. 2002, 41, 898.
15. S. Mondal, R. K. Mohamed, M. Manoharan, H. Phan, I. V. Alabugin, Org. Lett. 2013, 15, 5650.
16. Recent review on C-C fragmentations:, M. A. Drahl, M. Manpadi, L. J. Williams, Angew. Chem. 2013, 125, 11430
17. Angew. Chem. Int. Ed. 2013, 52, 11222.
18. B. Gold, G. B. Dudley, I. V. Alabugin, J. Am. Chem. Soc. 2013, 135, 1558
19. B. Gold, N. Shevchenko, N. Bonus, G. B. Dudley, I. V. Alabugin, J. Org. Chem. 2012, 77, 75
20. K. Gilmore, M. Manoharan, J. Wu, P. v. R. Schleyer, I. V. Alabugin, J. Am. Chem. Soc. 2012, 134, 10584.
21. D. Crich, A. Bowers, Org. Lett. 2006, 8, 4327
22. A. Baroudi, J. Alicea, P. Flack, J. Kirincich, I. V. Alabugin, J. Org. Chem. 2011, 76, 1521
23. A. Baroudi, P. Flack, I. V. Alabugin, Chem. Eur. J. 2010, 16, 12316
24. A. Baroudi, J. Alicea, I. V. Alabugin, Chem. Eur. J. 2010, 16, 7683
25. U. Wille, Chem. Rev. 2013, 113, 813
26. L. Debien, S. Zard, J. Am. Chem. Soc. 2013, 135, 3808
27. R. Heng, S. Z. Zard, Chem. Commun. 2011, 47, 3296
28. F. M. Kessabi, T. Winkler, J. A. R. Luft, K. N. Houk, Org. Lett. 2008, 10, 2255
29. J. A. R. Luft, T. Winkler, F. Murphy, F. M. Kessabi, K. N. Houk, J. Org. Chem. 2008, 73, 8175
30. B. Quiclet-Sire, S. Z. Zard, Beilstein J. Org. Chem. 2013, 9, 557.Similar transformation catalyzed by a radical S-Adenosyl methionine (SAM) enzyme
31. N. Mahanta; D. Fedoseyenko, T. Dairi, T. P. Begley, J. Am. Chem. Soc. 2013, 135, 15318
32. D. Fedoseyenko, T. Dairi, T. P. Begley, J. Am. Chem. Soc. 2013, 135, 15318.
33. S. J. Cole, J. N. Kirwan, B. P. Roberts, C. R. J. Willis, Chem. Soc. Perkin Trans. 1 1991, 103
34. B. P. Roberts, Chem. Soc. Rev. 1999, 28, 25
35. Y. Cai, B. P. J. Roberts, Chem. Soc. Perkin Trans. 2 2002, 1858
36. C. Chatgilialoglu, Organosilanes in Radical Chemistry, Wiley, New York, 2004
37. C. H. Schiesser, M. A. Skidmore, J. Chem. Soc. Perkin Trans. 2 1998, 2329
38. J. Guin, C. Mueck-Lichtenfeld, S. Grimme, A. Studer, J. Am. Chem. Soc. 2007, 129, 4498.
39. S. J. Blanksby, G. B. Ellison, Acc. Chem. Res. 2003, 36, 255.
40. D. Crich, D. Grant, V. Krishnamurthy, M. Patel, Acc. Chem. Res. 2007, 40, 453.
41. L. F. Loucks, K. J. Laidler, Can. J. Chem. 1967, 45, 2785.
42. I. V. Alabugin, M. Manoharan, T. A. Zeidan, J. Am. Chem. Soc. 2003, 125, 14014.
43. I. V. Alabugin, K. Gilmore, P. Peterson, WIREs Comput. Mol. Sci. 2011, 1, 109.
44. R. Hoffmann, Acc. Chem. Res. 1971, 4, 1
45. R. Gleiter, Angew. Chem. 1974, 86, 770
46. Angew. Chem. Int. Ed. Engl. 1974, 13, 696
47. M. N. Paddon-Row, Acc. Chem. Res. 1982, 15, 245
48. M. Abe, Chem. Rev. 2013, 113, 7011
49. R. Gleiter, G. Haberhauer, in Aromaticity and Other Conjugation Effects, Wiley-VCH, Weinheim, 2012.
50. R. K. Mohamed, P. W. Peterson, I. V. Alabugin, Chem. Rev. 2013, 113, 7089
51. I. V. Alabugin, M. Manoharan, J. Phys. Chem. A 2003, 107, 3363.
52. C. F. Logan, P. Chen, J. Am. Chem. Soc. 1996, 118, 2113
53. M. J. Schottelius, P. Chen, J. Am. Chem. Soc. 1996, 118, 4896
54. R. R. Squires, C. J. Cramer, J. Phys. Chem. A 1998, 102, 9072
55. E. Kraka, D. Cremer, J. Am. Chem. Soc. 2000, 122, 8245
56. F. C. Pickard IV, R. L. Shepherd, A. E. Gillis, M. E. Dunn, S. Feldgus, K. N. Kirschner, G. C. Shields, M. Manoharan, I. V. Alabugin, J. Phys. Chem. A 2006, 110, 2517.
57. A. M. Brouwer, J. M. Zwier, C. Svendsen, O. S. Mortensen, F. W. Langkilde, R. Wilbrandt, J. Am. Chem. Soc. 1998, 120, 3748
58. G. Balakrishnan, T. Keszthelyi, R. Wilbrandt, J. M. Zwier, A. M. Brouwer, W. J. Buma, J. Phys. Chem. A 2000, 104, 1834
59. S. Deb, X. Cheng, P. M. Weber, J. Phys. Chem. Lett. 2013, 4, 2780.
60. R. A. Marcus, J. Chem. Phys. 1956, 24, 966
61. R. A. Marcus, Annu. Rev. Phys. Chem. 1964, 15, 155
62. R. A. Marcus, J. Phys. Chem. 1968, 72, 891. For alternative models, see also
63. M. G. Evans, M. Polanyi, Trans. Faraday Soc. 1938, 34, 11
64. G. W. Koeppl, A. J. Kresge, J. Chem. Soc. Chem. Commun. 1973, 371.
65. I. V. Alabugin, M. Manoharan, J. Am. Chem. Soc. 2005, 127, 12583
66. I. V. Alabugin, M. Manoharan, J. Am. Chem. Soc. 2005, 127, 9534. For potential caveats, see
67. S. Osuna, K. N. Houk, Chem. Eur. J. 2009, 15, 13219.