Theoretical studies on the regioselectivity of iridium-catalyzed 1,3-dipolar azide-alkyne cycloaddition reactions

Journal of Organic Chemistry

Volumn 79, Issue 24, 2014, Pages 11970-11980

  Luo, Qiong ^a,b   Jia, Guochen ^a   Sun, Jianwei ^a   Lin, Zhenyang ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b SOUTH CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYSIS; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; HYDROCARBONS; IRIDIUM; LIGANDS; NITROGEN; POSITIVE IONS; REGIOSELECTIVITY;

AZIDE-ALKYNE CYCLOADDITION; CARBENE LIGANDS; CYCLOADDITION REACTION; OXIDATIVE COUPLINGS; REACTION MECHANISM; REDUCTIVE ELIMINATION; TERMINAL-NITROGEN; THEORETICAL STUDY;

REACTION INTERMEDIATES;

5 SULFENYLTRIAZOLE; ALKYNE; AZIDE; CARBENE; CARBON; IRIDIUM; NITROGEN; TRIAZOLE; UNCLASSIFIED DRUG; 4-BROMOTRIAZOLE; METHANE; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CYCLOADDITION; DENSITY FUNCTIONAL THEORY; ELIMINATION REACTION; ISOMERIZATION; OXIDATIVE COUPLING; REACTION ANALYSIS; STEREOCHEMISTRY; THEORETICAL STUDY; ANALOGS AND DERIVATIVES; CATALYSIS; CHEMISTRY;

ALKYNES; AZIDES; CATALYSIS; CYCLOADDITION REACTION; IRIDIUM; METHANE; MODELS, MOLECULAR; TRIAZOLES;

EID: 84919676487     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5018348     Document Type: Article

References (39)

1. (a) Fan, W.-Q.; Katritzky, A. R. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier Science: Oxford, U.K., 1996; Vol.4, pp 1-126.
2. (b) Manetsch, R.; Krasiski, A.; Radi, Z.; Raushel, J.; Taylor, P.; Sharpless, K. B.; Kolb, H. C. J. Am. Chem. Soc. 2004, 126, 12809.
3. (c) Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Chem. Rev. 2013, 113, 4905.
4. (d) Wang, J.; Sui, G.; Mocharla, V. P.; Lin, R. J.; Phelps, M. E.; Kolb, H. C.; Tseng, H.-R. Angew. Chem., Int. Ed. 2006, 45, 5276.
5. (e) Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Med. Res. Rev. 2008, 28, 278.
6. (a) Nandivada, H.; Jiang, X. W.; Lahann, J. Adv. Mater. 2007, 19, 2197.
7. (b) Lewis, J. E. M.; McAdam, C. J.; Gardinerb, M. G.; Crowley, J. D. Chem. Commun. 2013, 49, 3398.
8. (c) Golas, P. L.; Matyjaszewski, K. Chem. Soc. Rev. 2010, 39, 1338.
9. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
10. (b) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
11. (c) Miaoa, T.; Wang, L. Synthesis 2008, 363.
12. (d) Lipshutz, B. H.; Taft, B. R. Angew. Chem., Int. Ed. 2006, 45, 8235.
13. (e) Shin, J.-A.; Lim, Y.-G.; Lee, K.-H. J. Org. Chem. 2012, 77, 4117.
14. (a) Zhang, L.; Chen, X.; Xue, P.; Sun, H. H. Y.; Williams, I. D.; Sharpless, K. B.; Fokin, V. V.; Jia, G. J. Am. Chem. Soc. 2005, 127, 15998.
15. (b) Rasmussen, L. K.; Boren, B. C.; Fokin, V. V. Org. Lett. 2007, 9, 5337.
16. (c) Boren, B. C.; Narayan, S.; Rasmussen, L. K.; Zhang, L.; Zhao, H.; Lin, Z.; Jia, G.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 8923.
17. (d) Wang, D.; Salmon, L.; Ruiz, J.; Astruc, D. Chem. Commun. 2013, 49, 6956.
18. (a) McNulty, J.; Keskar, K.; Vemula, R. Chem.-Eur. J. 2011, 17, 14727.
19. (b) Hong, L.; Lin, W.; Zhang, F.; Liu, R.; Zhou, X. Chem. Commun. 2013, 49, 5589.
20. (c) Wang, Y.-C; Xie, Y.-Y.; Qu, H.-E.; Wang, H.-S.; Pan, Y.-M.; Huang, F.-P. J. Org. Chem. 2014, 79, 4463.
21. Worrell, B. T.; Malik, J. A.; Fokin, V. V. Science 2013, 340, 457.
22. Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210.
23. (a) Hein, J. E.; Tripp, J. C.; Krasnova, L. B.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2009, 48, 8018.
24. (b) Brotherton, W. S.; Clark, R. J.; Zhu, L. J. Org. Chem. 2012, 77, 6443.
25. Ding, S.; Jia, G.; Sun, J. Angew. Chem., Int. Ed. 2014, 53, 1877.
26. Rasolofonjatovo, E.; Theeramunkong, S.; Bouriaud, A.; Kolodych, S.; Chaumontet, M.; Taran, F. Org. Lett. 2013, 15, 4698.
27. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215.
28. (a) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
29. (b) Hays, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
30. (a) Fukui, K. J. Phys. Chem. 1970, 74, 4161.
31. (b) Fukui, K. Acc. Chem. Res. 1981, 14, 363.
32. Reed, A. E.; Weinhold, F. J. Chem. Phys. 1985, 83, 1736.
33. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378.
34. Frisch, M. J. et al. Gaussian 09, revision D.01; Gaussian, Inc., Wallingford CT, 2009.
35. Albright, T. A.; Burdett, J. K.; Whangbo, M.-H. Orbital Interactions in Chemistry, 2nd ed.; John Wiley & Sons: New York, 2013.
36. Lam, K. C.; Lam, W. H.; Lin, Z.; Marder, T. B.; Norman, N. C. Inorg. Chem. 2004, 43, 2541.
37. Cenini, S.; Gallo, E.; Caselli, A.; Ragaini, F.; Fantauzzi, S.; Piangiolino, C. Coord. Chem. Rev. 2006, 250, 1234.
38. Hartwig, J. F.; Cook, K. S.; Hapke, M.; Incarvito, C. D.; Fan, Y. B.; Webster, C. E.; Hall, M. B. J. Am. Chem. Soc. 2005, 127, 2538.
39. Wei, C. S.; Jiménez-Hoyos, C. A.; Videa, M. F.; Hartwig, J. F.; Hall, M. B. J. Am. Chem. Soc. 2010, 132, 3078.