"Two functional groups in one package": Using both alkyne π-bonds in cascade transformations

Journal of Organic Chemistry

Volumn 78, Issue 16, 2013, Pages 7777-7784

  Alabugin, Igor V ^a   Gold, Brian ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CASCADE TRANSFORMATIONS; DESIGN AND CONTROL; ORTHOGONALITY; RADICAL INITIATORS; RADICAL PROCESS;

CASCADE CONTROL SYSTEMS; FUNCTIONAL GROUPS;

HYDROCARBONS;

ALKENE; ALKYNE; CARBONYL DERIVATIVE; HYDROCARBON; NANORIBBON; RADICAL; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CLICK CHEMISTRY; COPE REARRANGEMENT; COVALENT BOND; CYCLIZATION; CYCLOADDITION; CYCLOPROPANATION; ELECTRON TRANSPORT; HYDROGENATION; PHOTOREACTIVITY; REACTOR CASCADE; THERMODYNAMICS;

ALKYNES; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 84882369119     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401091w     Document Type: Article

References (66)

1. Ess, D. H.; Jones, G. O.; Houk, K. N. Org. Lett. 2008, 10, 1633
2. Because of the lowering of the LUMO, bent alkynes are also good acceptors Ronan, N. G.; Domelsmith, L. N.; Houk, K. N.; Bowne, A. T.; Levin, R. H. Tetrahedron Lett. 1979, 20, 3237
3. Gold, B.; Dudley, G. B.; Alabugin, I. V. J. Am. Chem. Soc. 2013, 135, 1558
4. Gold, B.; Shevchenko, N. E.; Bonus, N.; Dudley, G. B.; Alabugin, I. V. J. Org. Chem. 2012, 77, 75
5. Alabugin, I. V.; Manoharan, M. J. Am. Chem. Soc. 2003, 125, 4495
6. Peterson, P. W.; Shevchenko, N.; Alabugin, I. V. Org. Lett. 2013, 15, 2238
7. Nicolaides, A.; Borden, W. T. J. Am. Chem. Soc. 1991, 113, 6750
8. Gilmore, K.; Manoharan, M.; Wu, J.; Schleyer, P.v.R; Alabugin, I. V. J. Am. Chem. Soc. 2012, 134, 10584
9. Byers, P.; Alabugin, I. V. J. Am. Chem. Soc. 2012, 134, 9609
10. For the development of "all-endo" cascades, see: Byers, P. M.; Rashid, J. I.; Mohamed, R. K.; Alabugin, I. V. Org. Lett. 2012, 14, 6032
11. Vasilyev, A. V. Russ. Chem. Rev. 2013, 82, 187
12. Wille, U. Chem. Rev. 2013, 113, 813
13. Utility of vinyl radicals for promoting a difficult reaction: Alabugin, I. V.; Timokhin, V. I.; Abrams, J. N.; Manoharan, M.; Ghiviriga, I.; Abrams, R. J. Am. Chem. Soc. 2008, 130, 10984
14. Vasilevsky, S. F.; Mikhailovskaya, T. F.; Mamatyuk, V. I.; Bogdanchikov, G. A.; Manoharan, M.; Alabugin, I. V. J. Org. Chem. 2009, 74, 8106
15. Gilmore, K.; Manoharan, M.; Wu, J. I.-C.; Schleyer, P. v. R.; Alabugin, I. V. J. Am. Chem. Soc. 2012, 134, 10584
16. Aromaticity can also be utilized as a tool for the better understanding of unusual reactions. For example, evolution of aromaticity identified a "missing" intermediate in the cyclization-mediated mechanism for Au-catalyzed Claisen rearrangements of alkynes and allenes: Vidhani, D. V.; Cran, J. W.; Krafft, M. E.; Manoharan, M.; Alabugin, I. V. J. Org. Chem. 2013, 78, 2059
17. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734
18. Gilmore, K.; Alabugin, I. V. Chem. Rev. 2011, 111, 6513
19. Alabugin, I. V.; Gilmore, K.; Manoharan, M. J. Am. Chem. Soc. 2011, 133, 12608
20. Cunje, A.; Rodriquez, C. F.; Lien, M. H.; Hopkinson, A. C. J. Org. Chem. 1996, 61, 5212
21. Collins, C. J.; Hanack, M.; Stutz, H.; Auchter, G.; Schoberth, W. J. Org. Chem. 1983, 48, 5260
22. Overman, L. E.; Sharp, M. J. J. Am. Chem. Soc. 1988, 110, 612
23. Johnson, R. P. J. Phys. Org. Chem. 2010, 23, 283
24. Hoye, T. R.; Baire, B.; Niu, D.; Willoughby, P. H.; Woods, B. P. Nature 2012, 490, 208
25. Karmakar, R.; Mamidipalli, P.; Yun, S. Y.; Lee, D. Org. Lett. 2013, 15, 1938
26. Bergman, R. G. Acc. Chem. Res. 1973, 6, 25
27. Graulich, N.; Hopf, H.; Schreiner, P. R. Chem. Soc. Rev. 2010, 39, 1503
28. Mohamed, R. K.; Peterson, P. W.; Alabugin, I. V. Chem. Rev. 2013, http://dx.doi.org/10.1021/cr4000682
29. Grissom, J. W.; Klingberg, D.; Huang, D.; Slattery, B. J. J. Org. Chem. 1997, 62, 603
30. Roy, S.; Anoop, A.; Biradha, K.; Basak, A. Angew. Chem., Int. Ed. 2011, 50, 8316
31. Lewis, K. D.; Matzger, A. J. J. Am. Chem. Soc. 2005, 127, 9968
32. Nechab, M.; Campolo, D.; Maury, J.; Perfetti, P.; Vanthuyne, N.; Siri, D.; Bertrand, M. P. J. Am. Chem. Soc. 2010, 132, 14742
33. Baroudi, A.; Mauldin, J.; Alabugin, I. V. J. Am. Chem. Soc. 2010, 132, 967
34. Baroudi, A.; Alicea, J.; Flack, P.; Kirincich, J.; Alabugin, I. V. J. Org. Chem. 2011, 76, 1521
35. Graulich, N.; Hopf, H.; Schreiner, P. R. Chem. Soc. Rev. 2010, 39, 1503
36. Stepanov, A. A.; Gornostaev, L. M.; Vasilevsky, S. F.; Arnold, E. V.; Mamatyuk, V. I.; Fadeev, D. S.; Gold, B.; Alabugin, I. V. J. Org. Chem. 2011, 76, 8737
37. Poloukhtine, A.; Rassadin, V.; Kuzmin, A.; Popik, V. V. J. Org. Chem. 2010, 75, 5953
38. Peterson, P. W.; Mohamed, R. K.; Alabugin, I. V. Eur. J. Org. Chem. 2013, 2013, 2505
39. Perrin, C. L.; Rodgers, B. L.; O'Connor, J. M. J. Am. Chem. Soc. 2007, 129, 4795
40. Myers, A. G.; Dragovich, P. S.; Kuo, E. Y. J. Am. Chem. Soc. 1992, 114, 9369
41. Hughes, T. S.; Carpenter, B. K. J. Chem. Soc., Perkin Trans. 2 1999, 2291
42. Carpenter, B. K. Chem. Rev. 2013, http://pubs.acs.org/doi/abs/10.1021/ cr300511u
43. Kar, M.; Basak, A. Chem. Rev. 2007, 107, 2861
44. Prall, M.; Wittkopp, A.; Schreiner, P. R. J. Phys. Chem. A. 2001, 105, 9265
45. Vavilala, C.; Byrne, N.; Kraml, C. M.; Ho, D. M.; Pascal, R. A. J. Am. Chem. Soc. 2008, 130, 13549
46. Whitlock, H. W., Jr.; Sandvick, P. E.; Overman, L. E.; Reichardt, P. B. J. Org. Chem. 1969, 34, 879
47. Alabugin, I. V.; Kovalenko, S. V. J. Am. Chem. Soc. 2002, 124, 9052
48. Yang, W.-Y.; Breiner, B.; Kovalenko, S. V.; Ben, C.; Singh, M.; LeGrand, S. N.; Sang, A. Q.-X.; Strouse, G. F.; Copland, J. A.; Alabugin, I. V. J. Am. Chem. Soc. 2009, 131, 11458
49. Yang, W.-Y.; Roy, S.; A, R.; Phrathep, B.; Rengert, Z.; Alabugin, I. V. J. Med. Chem. 2011, 54, 8501
50. Breiner, B.; Kaya, K.; Roy, S.; Yang, W.-Y.; Alabugin, I. V. Org. Biomol. Chem. 2012, 10, 3974
51. Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208
52. Curran, D. P.; Kim, D.; Liu, H. T.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900
53. Beaufils, F.; Dénès, F.; Becattini, B.; Renaud, P.; Schenk, K. Adv. Synth. Catal. 2005, 347, 1587
54. Alabugin, I. V.; Gilmore, K.; Patil, S.; Manoharan, M.; Kovalenko, S. V.; Clark, R. J.; Ghiviriga, I. J. Am. Chem. Soc. 2008, 130, 11535
55. Takahashi, M.; Kitahara, Y.; Murata, I.; Nitta, T.; Woods, M. C. Tetrahedron Lett. 1968, 30, 3387
56. Zeidan, T.; Kovalenko, S. V.; Manoharan, M.; Clark, R. J.; Ghiviriga, I.; Alabugin, I. V. J. Am. Chem. Soc. 2005, 127, 4270
57. Yang, W.-Y.; Marrone, S. A.; Minors, N.; Zorio, D. A. R.; Alabugin, I. V. Beilst. J. Org. Chem. 2011, 7, 813
58. For an example where regioselectivity of carbometallation/oxidation sequences is controlled via oxidation of the initially formed Cu-C bond, see: Minko, Y.; Pasco, M.; Lercher, L.; Botoshansky, M.; Marek, I. Nature 2012, 490, 522
59. Vasilevsky, S. F.; Baranov, D. S.; Mamatyuk, V. I.; Gatilov, Y. V.; Alabugin, I. V. J. Org. Chem. 2009, 74, 6143
60. Baranov, D.; Gold, B.; Vasilevsky, S.; Alabugin, I. V. J. Org. Chem. 2013, 78, 2074
61. Roy, S.; Davydova, M. P.; Pal, R.; Gilmore, K.; Tolstikov, G. A.; Vasilevsky, S. F.; Alabugin, I. V. J. Org. Chem. 2011, 76, 7482
62. Shindo, M.; Sato, Y.; Yoshikawa, T.; Koretsune, R.; Shishido, K. J. Org. Chem. 2004, 69, 3912
63. You, L.; Al-Rashid, Z. F.; Figueroa, R.; Ghosh, S. K.; Li, G.; Lu, T.; Hsung, R. P. Synlett 2007, 1656
64. Engel, D. A.; Dudley, G. B. Org. Biomol. Chem. 2009, 7, 4149
65. Kivala, M.; Diederich, F. Acc. Chem. Res. 2009, 42, 235
66. Pal, R.; Clark, R. J.; Manoharan, M.; Alabugin, I. V. J. Org. Chem. 2010, 75, 8689