Mechanistic studies on the Cu-catalyzed three-component reactions of sulfonyl azides, 1-alkynes and amines, alcohols, or water: Dichotomy via a common pathway

Journal of Organic Chemistry

Volumn 73, Issue 14, 2008, Pages 5520-5528

  Eun, Jeong Yoo ^a   Ahlquist, Mårten ^b   Bae, Imhyuck ^a   Sharpless, K Barry ^b   Fokin, Valery V ^b   Chang, Sukbok ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALKYLATION; AMIDES; AMINATION; AMINES; CHEMICAL BONDS; CHEMICAL REACTIONS; COPPER ALLOYS; CYCLOADDITION; HYDROCARBONS; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS;

1-ALKYNES; AMERICAN CHEMICAL SOCIETY (ACS); CHEMICAL EQUATIONS; COMMON PATHWAY; COMPUTATIONAL STUDIES; CYCLOADDITION REACTIONS; EXPERIMENTAL DATA; IMIDATES; KETENIMINE; KEY INTERMEDIATES; MECHANISTIC PATHWAYS; MECHANISTIC STUDIES; PRODUCT DISTRIBUTIONS; SULFONYL AZIDES; TERMINAL ALKYNES; THREE-COMPONENT; THREE-COMPONENT REACTIONS; TRIPLE BONDS;

COPPER;

1 (4 METHYLBENZENESULFONYL) 4 PHENYL 5 IODO 1,2,3 TRIAZOLE; ALCOHOL DERIVATIVE; ALKYNE DERIVATIVE; AMIDE; AMIDINE; AMINE; AZIDE; COPPER; TRIAZOLE DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CYCLOADDITION;

ALCOHOLS; ALKYNES; AMINES; AZIDES; CATALYSIS; COPPER; ETHYLENES; IMIDOESTERS; ISOMERISM; KETONES; KINETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SULFUR COMPOUNDS; TEMPERATURE; TRIAZOLES; WATER;

EID: 48249116347     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800733p     Document Type: Article

References (70)

1. Bunce, R. A. Tetrahedron 1995, 51, 13103-13159.
2. (a) de Meijere, A.; von Zezschwitz, P.; Nüske, H.; Stulgies, B. J. Organomet. Chem. 2002, 653, 129-140.
3. (b) Bruggink, A.; Schoevaart, R.; Kieboom, T. Org. Process Res. Dev. 2003, 7, 622-640.
4. (c) Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33, 302-312.
5. (d) Yoshida, M. J. Pharm. Soc. Jpn. 2004, 124, 425-435.
6. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
7. (b) Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
8. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
9. (a) Bae, I.; Han, H.; Chang, S. J. Am. Chem. Soc. 2005, 127, 2038-2039.
10. (b) Kim, S. H.; Jung, D. Y.; Chang, S. J. Org. Chem. 2007, 72, 9769-9771.
11. (c) Kim, J. Y.; Kim, S. H.; Chang, S. Tetrahedron Lett. 2008, 49, 1745-1749.
12. Yoo, E. J.; Bae, I.; Cho, S. H.; Han, H.; Chang, S. Org. Lett. 2006, 8, 1347-1350.
13. (a) Cho, S. H.; Yoo, E. J.; Bae, I.; Chang, S. J. Am. Chem. Soc. 2005, 127, 16046-16047.
14. (b) Cho, S. H.; Chang, S. Angew. Chem., Int. Ed. 2007, 46, 1897-1900.
15. (c) Cho, S. H.; Hwang, S. J.; Chang, S. Org. Synth. 2008, 85, 131-137.
16. (d) Cho, S. H.; Chang, S. Angew. Chem., Int. Ed. 2008, 47, 2836-2839.
17. Greenhill, J. V.; Lue, P. Prog. Med. Chem. 1993, 30, 203-326.
18. (a) Boyd, G. V. In The Chemistry of Amidines and Imidates; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1991; Vol. 2,Chapter 8.
19. (b) Barker, J.; Kilner, M. Coord. Chem. Rev. 1994, 133, 219-300.
20. (c) Birman, V. B.; Li, X.; Han, Z. Org. Lett. 2007, 9, 37-40.
21. (a) Neilson, D. G. In The Chemistry of Amdines and Imidates; Patai, S., Ed.; John Wiley & Sons: London, UK, 1975; Chapter 8.
22. (b) Kantlehner, W. Synthesis of Iminium Salts, Orthoesters and Related Compounds. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 2, pp 485-599.
23. (c) Kochi, T.; Ellman, J. A. J. Am. Chem. Soc. 2004, 126, 15652-15653.
24. Humphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243-2266.
25. (a) Whiting, M.; Fokin, V. V. Angew. Chem., Int. Ed. 2006, 45, 3157-3161.
26. (b) Xu, X.; Cheng, D.; Li, J.; Guo, H.; Yan, J. Org. Lett. 2007, 9, 1585-1587.
27. Cui, S.-L.; Lin, X.-F.; Wang, Y.-G. Org. Lett. 2006, 8, 4517-4520.
28. Yoo, E. J.; Chang, S. Org. Lett. 2008, 10, 1163-1166.
29. Jin, Y.; Fu, H.; Yin, Y.; Jiang, Y.; Zhao, Y. Synlett 2007, 901-904.
30. Rodima, T.; Kaljurand, I.; Pihl, A.; Maemets, V.; Leito, I.; Koppel, I. A. J. Org. Chem. 2002, 67, 1873-1881.
31. For details, see the Supporting Information.
32. Suárez, A.; Fu, G. C. Angew. Chem., Int. Ed. 2004, 43, 3580-3582.
33. Raap, R. Can. J. Chem. 1971, 49, 1792-1798.
34. (a) Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210-216.
35. (b) Rodionov, V. O.; Fokin, V. V.; Finn, M. G. Angew. Chem., Int. Ed. 2005, 44, 2210-2215.
36. Wu, Y.-M.; Deng, J.; Li, Y.; Chen, Q.-Y. Synthesis 2005, 8, 1314-1318.
37. Cassidy, M. P.; Raushel, J.; Fokin, V. V. Angew. Chem., Int. Ed. 2006, 45, 3154-3157.
38. Differding, E.; Ghosez, L. Tetrahedron Lett. 1985, 26, 1647-1650.
39. (a) Motoyoshiya, J.; Teranishi, A.; Mikoshiba, R.; Yamamoto, I.; Gotoh, H.; Enda, J.; Ohshiro, Y.; Agawa, T. J. Org. Chem. 1980, 45, 5385-5387.
40. (b) Sung, K.; Wu, S.-H.; Wu, R.-R.; Sun, S.-Y. J. Org. Chem. 2002, 67, 4298-4303.
41. Sauers, R. R.; Van Arnum, S. D. Phosphorus, Sulfur, and Silicon 2003, 178, 2169-2181.
42. Bendikov, M.; Duong, H. M.; Bolanos, E.; Wudl, F. Org. Lett. 2005, 7, 783-786.
43. Yoo, E.; Ahlquist, M.; Kim, S. H.; Bae, I.; Fokin, V. V.; Sharpless, K. B.; Chang, S. Angew. Chem., Int. Ed. 2007, 46, 1730-1733.
44. (a) Brown, D. J.; Harper, J. S. J. Chem. Soc. 1963, 1276-1284.
45. (b) Perrin, D. D. J. Chem. Soc. 1963, 1284-1290.
46. (c) Gilchrist, T. L.; Gymer, G. E. Adv. Heterocycl. Chem. 1974, 16, 33-85.
47. (d) Gilchrist, T. L. Adv. Heterocycl. Chem. 1987, 41, 41-74.
48. (e) Fujii, T.; Itaya, T. Heterocycles 1998, 48, 359-390.
49. (f) Katritzky, A. R.; Ji, F. B.; Fan, W.-Q.; Gallos, J. K.; Greenhill, J. V.; King, R. W.; Steel, P. J. J. Org. Chem. 1992, 57, 190-195.
50. (g) Boivin, J.; Huppé, S.; Zard, S. Z. Tetrahedron Lett. 1995, 36, 5737-5740.
51. Kirmse, W. Eur. J. Org. Chem. 2002, 2193-2256.
52. (a) Hermes, M. E.; Marsh, F. D. J. Am. Chem. Soc. 1967, 89, 4760-4764.
53. (b) Harmon, R. E.; Stanley, F.; Gupta, S. K.; Johnson, J. J. Org. Chem. 1970, 35, 3444-3448.
54. (a) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104-114.
55. (b) Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368-3398.
56. (c) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673-686.
57. (d) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079-3160.
58. (e) Odom, A. L. Dalton Trans. 2005, 225-233.
59. (a) Croce, P. D.; Stradi, R. Tetrahedron 1977, 33, 865-867.
60. (b) Fioravanti, S.; Pellacani, L.; Ricci, D.; Tardella, P. A. Tetrahedron: Asymmetry 1997, 8, 2261-2266.
61. (c) Xu, Y.; Wang, Y.; Zhu, S. Synthesis 2000, 513-516.
62. (d) Xu, Y.; Zhu, S. Tetrahedron 2001, 57, 4337-4341.
63. (a) Evans, D. A.; Bilodeau, M. T.; Faul, M. M. J. Am. Chem. Soc. 1994, 116, 2742-2753.
64. (b) Diaz-Requejo, M. M.; Perez, P. J.; Brookhart, M.; Templeton, J. L. Organometallics 1997, 16, 4399-4402.
65. Peterson, L. I.; Britton, E. C. Tetrahedron Lett. 1968, 9, 5357-5360.
66. Qian, H.; Shao, L.-X.; Huang, X. Synlett 2001, 1571-1572.
67. Helwig, R.; Hanack, M. Chem. Ber. 1985, 118, 1008-1021.
68. 39 it was illustrated how a second copper atom could stabilize the cycloaddition transition state as well as the following intermediate, explaining the observed second order dependence of copper on the rate. In the current study we will mainly discuss mononuclear copper acetylides, since the interest is to compare the reactivity of N-sulfonyl azides to the N-alkyl analogues (Figure Presented)
69. -1). This further shows that stronger σ-donors favor dicoordinate copper(I) centers.
70. Ahlquist, M.; Fokin, V. V. Organometallics 2007, 26, 4389-4391.