Reaction progress kinetic analysis of a copper-catalyzed aerobic oxidative coupling reaction with N-phenyl tetrahydroisoquinoline

Journal of Organic Chemistry

Volumn 79, Issue 24, 2014, Pages 12033-12040

  Scott, Martin ^b   Sud, Abhishek ^a   Boess, Esther ^a   Klussmann, Martin ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^b UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSTS; CHEMICAL ACTIVATION; CHEMICAL COMPOUNDS; KINETICS; NUCLEOPHILES; OXIDANTS; SUBSTRATES;

ADDITIONAL EXPERIMENTS; CATALYZED REACTIONS; KINETIC INVESTIGATIONS; OXIDATIVE COUPLING REACTIONS; REACTION PROGRESS; SILYL ENOL ETHERS; TERT-BUTYLHYDROPEROXIDE; TETRAHYDROISOQUINOLINES;

CATALYSIS;

COPPER; NUCLEOPHILE; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; CALORIMETRY; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; DISSOCIATION; ELECTRON TRANSPORT; MOLECULE; OXIDATION; OXIDATIVE COUPLING; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; REACTION TIME;

EID: 84919684298     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5018876     Document Type: Article

References (59)

1. Girard, S. A.; Knauber, T.; Li, C.-J. Angew. Chem., Int. Ed. 2014, 53, 74-100
2. Zheng, C.; You, S.-L. RSC Adv. 2014, 4, 6173-6214
3. Jia, F.; Li, Z. Org. Chem. Front. 2014, 1, 194-214
4. Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3464-3484
5. Rohlmann, R.; Mancheño, O. G. Synlett 2013, 24, 6-10
6. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215-1292
7. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780-1824
8. Klussmann, M.; Sureshkumar, D. Synthesis 2011, 353-369
9. Scheuermann, C. J. Chem.-Asian J. 2010, 5, 436-451
10. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677-685
11. Sarhan, A. A. O.; Bolm, C. Chem. Soc. Rev. 2009, 38, 2730-2744
12. Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439-2463
13. Gulzar, N.; Schweitzer-Chaput, B.; Klussmann, M. Catal. Sci. Technol. 2014, 4, 2778-2796
14. Shi, Z.; Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3381-3430
15. Campbell, A. N.; Stahl, S. S. Acc. Chem. Res. 2012, 45, 851-863
16. Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062-11087
17. Qin, Y.; Lv, J.; Luo, S. Tetrahedron Lett. 2014, 55, 551-558
18. Jones, K. M.; Klussmann, M. Synlett 2012, 23, 159-162
19. Ravelli, D.; Fagnoni, M. ChemCatChem 2012, 4, 169-171
20. Murata, S.; Miura, M.; Nomura, M. Chem. Commun. 1989, 116-118
21. Murahashi, S.-I.; Komiya, N.; Terai, H.; Nakae, T. J. Am. Chem. Soc. 2003, 125, 15312-15313
22. Baslé, O.; Li, C.-J. Green Chem. 2007, 9, 1047-1050
23. Shen, Y.; Tan, Z.; Chen, D.; Feng, X.; Li, M.; Guo, C.-C.; Zhu, C. Tetrahedron 2009, 65, 158-163
24. Singhal, S.; Jain, S. L.; Sain, B. Chem. Commun. 2009, 2371-2372
25. Alagiri, K.; Prabhu, K. R. Org. Biomol. Chem. 2012, 10, 835-842
26. Xie, J.; Li, H.; Zhou, J.; Cheng, Y.; Zhu, C. Angew. Chem., Int. Ed. 2012, 51, 1252-1255
27. Hu, J.; Wang, J.; Nguyen, T. H.; Zheng, N. Beilstein J. Org. Chem. 2013, 9, 1977-2001
28. Cheng, G.-J.; Song, L.-J.; Yang, Y.-F.; Zhang, X.; Wiest, O.; Wu, Y.-D. ChemPlusChem 2013, 78, 943-951
29. Ratnikov, M. O.; Doyle, M. P. J. Am. Chem. Soc. 2013, 135, 1549-1557
30. Yamaguchi, K.; Wang, Y.; Mizuno, N. ChemCatChem 2013, 5, 2835-2838
31. Tsang, A. S.-K.; Jensen, P.; Hook, J. M.; Hashmi, A. S. K.; Todd, M. H. Pure Appl. Chem. 2011, 83, 655-665
32. Baslé, O.; Borduas, N.; Dubois, P.; Chapuzet, J. M.; Chan, T.-H.; Lessard, J.; Li, C.-J. Chem.-Eur. J. 2010, 16, 8162-8166
33. Wang, M.-Z.; Zhou, C.-Y.; Wong, M.-K.; Che, C.-M. Chem.-Eur. J. 2010, 16, 5723-5735
34. Murahashi, S.-I.; Naota, T.; Yonemura, K. J. Am. Chem. Soc. 1988, 110, 8256-8258
35. Boess, E.; Sureshkumar, D.; Sud, A.; Wirtz, C.; Farès, C.; Klussmann, M. J. Am. Chem. Soc. 2011, 133, 8106-8109
36. Boess, E.; Schmitz, C.; Klussmann, M. J. Am. Chem. Soc. 2012, 134, 5317-5325
37. Sureshkumar, D.; Sud, A.; Klussmann, M. Synlett 2009, 1558-1561
38. Murata, S.; Teramoto, K.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1993, 66, 1297-1298
39. Nishino, M.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2011, 76, 6447-6451
40. Tanoue, A.; Yoo, W.-J.; Kobayashi, S. Adv. Synth. Catal. 2013, 355, 269-273
41. Nelsen, S. F.; Ippoliti, J. T. J. Am. Chem. Soc. 1986, 108, 4879-4881
42. Blackmond, D. G. Angew. Chem., Int. Ed. 2005, 44, 4302-4320
43. Mathew, J. S.; Klussmann, M.; Iwamura, H.; Valera, F.; Futran, A.; Emanuelsson, E. A. C.; Blackmond, D. G. J. Org. Chem. 2006, 71, 4711-4722
44. Zotova, N.; Valera, F.; Blackmond, D. G. Chem. Ind. 2009, 123, 445-454
45. LeBlond, C.; Wang, J.; Larsen, R. D.; Orella, C. J.; Forman, A. L.; Landau, R. N.; Laquidara, J.; Sowa, J. R.; Blackmond, D. G.; Sun, Y. K. Thermochim. Acta 1996, 289, 189-207
46. Ferretti, A. C.; Mathew, J. S.; Blackmond, D. G. Ind. Eng. Chem. Res. 2007, 46, 8584-8589
47. El-Sayed, M. A.; Salam, A. H. A.; Abo-El-Dahab, H. A.; Refaat, H. M.; El-Dissouky, A. L. I. J. Coord. Chem. 2009, 62, 1015-1024
48. El-Sayed, M. A.; El-Toukhy, A.; Davies, G. Inorg. Chem. 1985, 24, 3387-3390
49. Baslé, O.; Li, C.-J. Chem. Commun. 2009, 4124-4126
50. Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810-11811
51. Li, Z.; Bohle, D. S.; Li, C.-J. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 8928-8933
52. Zhao, L.; Li, C.-J. Angew. Chem., Int. Ed. 2008, 47, 7075-7078
53. Simmons, E. M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 3066-3072
54. Toshiaki, W.; Yasuhiro, F.; Naoko, H.; Taro, S.; Yuji, Y.; Toru, H.; Takashi, O.; Akihiko, T.; Junichi, K.; Tadashi, O.; Keiko, T.; Kazumasa, N.; Shinichi, H.; Norihiro, U. Integrin expression inhibitors. U.S. Patent EP1258252 (A1), 2002.
55. Mohamed, M. A.; Yamada, K.-i.; Tomioka, K. Tetrahedron Lett. 2009, 50, 3436-3438
56. Chen, L.; Zhang, L.; Lv, J.; Cheng, J.-P.; Luo, S. Chem.-Eur. J. 2012, 18, 8891-8895
57. Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2005, 127, 6968-6969
58. For a discussion of the concept of rate-controlling steps, see: Laidler, K. J. J. Chem. Educ. 1988, 65, 250
59. Gottlieb, H. E.; Kotlyar, V.; Nudelmann, A. J. Org. Chem. 1997, 62, 7512-7515